Process for preparing alkyl esters of dl-cis chrysanthemic acid 机翻标题: 暂无翻译,请尝试点击翻译按钮。

公开号/公开日
EP0007828 A1 1980-02-06 [EP---7828]EP0007828 B1 1981-11-04 [EP---7828] / 1980-02-061981-11-04
申请号/申请日
1979EP-0400443 / 1979-06-29
发明人
FRANCK-NEUMANN, MICHEL;DIETRICH-BUCHECKER, CHRISTIANE;MIESCH, MICHEL;
申请人
ROUSSEL UCLAF;
主分类号
IPC分类号
A01N-053/10C07C-067/30C07C-067/303C07C-069/743C07C-069/747C07D-231/06
摘要
(EP---7828) Abstract in publication language, translation not available  L'invention concerne un procédé de préparation des composés dans laquelle R est un alcoyle de 1 à 6 carbones, consistant essentiellement soit à réduire le dérivé cyclopropénique correspondant: lui-même obtenu par irradiation des composés pyrazoliques: soit à irradier ou traiter par <FF>chauffage<FF> le composé pyrazolique préalablement réduit de formule:  Les composés I sont des intermédiaires dans la synthèse de composés insecticides bien connus.
机翻摘要
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地址
代理人
代理机构
;
优先权号
1978FR-0021814 1978-07-24
主权利要求
(EP---7828)  1. . Method of preparation of alkyl esters of the 2.2-dimethyl acid 3 ES (2 - methyl 1 - propenyl) cyclopropane-1 SR - carboxylic or alkyl esters of the acid dl cis chrysan-themic, esters of formula (I): HORN (I) \.dans which R represents a radical comprising alkyl from 1 to 6 carbon atoms, characterized in that in fact D of acting 3.3-dimethyl 2 (2 - methyl 1 - propenyl) 1-alcoxy because bonyl cyclopropene of foraule (VI): in which H preserves the above mentioned significance, with one. reducing agent selected in the group consisted hydrogen in the presence of "palladium or nickel boride deposited 15 on calcium carbonate and the diisiide. 2. Proceeded of preparation according to claim 1, characterized in that hydrogenation is carried out in the presence of nickel boride "Rain", prepared, in situ, according to the method of A. C. BROWN J. Org. Chem. -3jj 1900 (1970). 3. Proceeded of preparation according to claim 1, characterized in that the reducing agent is the diiraide, prepared according to the method of E. E. VAN MT. MELZN and Coll J. Amec. Chem. Plowshare 83.3725 (1961). 4. Method of preparation according to claim 1, characterized in that the 3,3-aimethyl 2 (2 - methyl 1 - propenyl) 1-alcoxy carbonyl cyclopropene (VI) is obtained while making react the methyl lithium with 2-methyl pent-2-4yne (II): then by subjecting the resulting derivative lithien, with the action of a chlorof ormiate of alkyl, to obtain an alkyl ester of the oique acid 5-iaethyl hex-A in 2-yne (III) of foraule: (III) in which E is defined conme with claim 1, then while making react this compound with diazo-2-propane gas, lice to obterir one. mix methyl ester of the acid 3,3-dimeth7l 5 (2-methyl 1-propenyl) 3:00 - pyrazole A-carbozylique (IV): 15 and of methyl ester of the 3.3-dimethyl acid 4 (2-meth7l 1-propenyl) I-pyrazole 5-cibox7lic (V) '.que one separate, if necessary, then by subjecting the compound of formula IV, the compound of formula V or their mixture with an irradiation, then by insulating cccpose the VI expected. 5. Method of preparation according to claim 4, characterized in that methyl ester of the acid 5-niethyl. hes-4-2-yne oique is obtained by introducing an ethereal solution of derived lithien 2-methyl pent-2-4-yne with - 55C5 +, 2OC, in an ethereal solution of methyl chlcroforaiate. 6. Method of preparation according to the claim, characterized in that the methyl mixture of ester of the 3.3-dimethyl acid 5 (2-methyl 1-propenyl) 3:00 - pyrazole 4carboxylic and of methyl ester of the 3.5-dimethyl acifie 4 (2-methyl 10 1-propenyl) 3:00 - pyrazole 5-carboxylic is obtained while introducing with - 6OC +. 20C, an ethereal solution of diazo-2-propane gas in methyl ester an ethereal solution of the acid oique 5-methyl hex4 2-yne. 7. Method of preparation according to claim 4.15 characterized in that the 3>3-dimethyl 2 (2 - niethyl 1 - propenyl) 1 (methoxy carbonyl) cyclopropene is obtained by irradiation by using a mercury discharge lamp PEZLIPS HPE 125, while operating with + 15 Channel +. 10C. 8. Alternative of the method of preparation of esters of formula I, as defined in claim 1, characterized in that one subjects a compound of formula (III): O F " øT F C F F TTT v cheap W W" wv iLT L Have J in which E is defined cam with claim 1, with the action of a reducing agent, to obtain a compound of formula (VIII): C/i LJ/ij fT-f R \ W F \ I "I WHOLE" I "wH" wHil VW Xi L there J--LL IHjCT (Z) which one makes act with dia20-2-propane gas, to obtain a mixture of alkyl ester of the 3.3-dimethyl acid cis 4,5-dihydro 5 (2-methyl 1-propenyl) A-Carboxylic JH-pyrazole (3Z): CH.,/and of alkyl ester of the acid 4,5-aihycro 5>5-oineth 4 (2-Eiethyl 1-propenyl)". 5-carboxylic H-pyrasole (I) Which one separates, then sounet conpose of foraule (ZI) with iiae irradiation or the action of heat, to obtain the compound of formula (I): 9. Proceeded according to the claim ø, characterized in that 10 the reducing agent that one makes act on the compound (II) is hydrogen in the presence of catalyst of Lindlar.
法律状态
(EP---7828) LEGAL DETAILS FOR EP0007828  Actual or expected expiration date=1999-06-29    Legal state=DEAD    Status=EXPIRED     Event publication date=1979-06-29  Event code=EP/APP  Event indicator=Pos  Event type=Examination events  Application details  Application country=EP EP79400443  Application date=1979-06-29  Standardized application number=1979EP-0400443     Event publication date=1980-02-06  Event code=EP/A1  Event type=Examination events  Application published with search report  Publication country=EP  Publication number=EP0007828  Publication stage Code=A1  Publication date=1980-02-06  Standardized publication number=EP---7828     Event publication date=1980-02-06  Event code=EP/AK  Event indicator=Pos  Event type=Designated states  Designated contracting states: Benannte vertragsstaaten CH DE FR GB NL    Event publication date=1980-07-09  Event code=EP/17P  Event indicator=Pos  Event type=Examination events  Request for examination filed Pruefungsantrag gestellt    Event publication date=1981-11-04  Event code=EP/B1  Event indicator=Pos  Event type=Event indicating In Force  Patent specification  Publication country=EP  Publication number=EP0007828  Publication stage Code=B1  Publication date=1981-11-04  Standardized publication number=EP---7828     Event publication date=1981-11-04  Event code=EP/AK  Event indicator=Pos  Event type=Designated states  Designated contracting states: Benannte vertragsstaaten CH DE FR GB NL    Event publication date=1999-06-29  Event code=EP/EEDX  Event indicator=Neg  Event type=Event indicating Not In Force  Patent has expired MEMBER STATE LEGAL DETAILS FOR CH  Actual or expected expiration date=1991-06-30    Legal state=DEAD    Status=EXPIRED   Corresponding cc:  Designated or member state=CH     Event publication date=1990-07-12  Event code=EP/PGFP  Event indicator=Pos  Event type=Event indicating In Force  Event type=Payment or non-payment notifications  Postgrant: annual fees paid to national office   Annual fees payment date=1990-07-12     Year of payment of annual fees=12  Corresponding cc:  Designated or member state=CH     Event publication date=1991-06-30  Event code=EP/PG25  Event indicator=Neg  Event type=Event indicating Not In Force  Event type=Payment or non-payment notifications  Lapsed in a contracting state announced via postgrant inform. from nat. office to EPO Corresponding cc:  Designated or member state=CH   Effective date of the event=1991-06-30     Event publication date=1992-02-28  Event code=EP/REG  Event code=CH/PL  Event indicator=Neg  Event type=Event indicating Not In Force  Reference to a national code Patent ceased Loeschung/radiation/radiazion Corresponding cc:  Designated or member state=CH  MEMBER STATE LEGAL DETAILS FOR DE2961231  Actual or expected expiration date=1992-04-01    Legal state=DEAD    Status=LAPSED   Corresponding cc:  Designated or member state=DE Corresponding appl: DE2961231  Application date in the designated or member state=1979-06-29   Application number in the designated or member state=1979DE-2961231 Corresponding cc:  Designated or member state=DE Corresponding pat: DE2961231  Publication stage code in the designated or member state=D1  Publication date in the designated or member state=1982-01-14   Publication number in the designated or member state=DE2961231    Event publication date=1982-01-14  Event code=EP/REF  Event type=Entry into national phase  Corresponds to: Corresponding cc:  Designated or member state=DE     Event publication date=1990-08-16  Event code=EP/PGFP  Event indicator=Pos  Event type=Event indicating In Force  Event type=Payment or non-payment notifications  Postgrant: annual fees paid to national office   Annual fees payment date=1990-08-16     Year of payment of annual fees=12  Corresponding cc:  Designated or member state=DE     Event publication date=1992-04-01  Event code=EP/PG25  Event indicator=Neg  Event type=Event indicating Not In Force  Event type=Payment or non-payment notifications  Lapsed in a contracting state announced via postgrant inform. from nat. office to EPO Corresponding cc:  Designated or member state=DE   Effective date of the event=1992-04-01  MEMBER STATE LEGAL DETAILS FOR FR  Actual or expected expiration date=1993-02-26    Legal state=DEAD    Status=LAPSED   Corresponding cc:  Designated or member state=FR     Event publication date=1991-06-25  Event code=EP/PGFP  Event indicator=Pos  Event type=Event indicating In Force  Event type=Payment or non-payment notifications  Postgrant: annual fees paid to national office   Annual fees payment date=1991-06-25     Year of payment of annual fees=13  Corresponding cc:  Designated or member state=FR     Event publication date=1993-02-26  Event code=EP/PG25  Event indicator=Neg  Event type=Event indicating Not In Force  Event type=Payment or non-payment notifications  Lapsed in a contracting state announced via postgrant inform. from nat. office to EPO Corresponding cc:  Designated or member state=FR   Effective date of the event=1993-02-26     Event publication date=1993-04-30  Event code=EP/REG  Event code=FR/ST  Event indicator=Neg  Event type=Event indicating Not In Force  Event type=Payment or non-payment notifications  Reference to a national code Notification of lapse Constatation de decheances Corresponding cc:  Designated or member state=FR  MEMBER STATE LEGAL DETAILS FOR GB  Actual or expected expiration date=1991-06-29    Legal state=DEAD    Status=LAPSED   Corresponding cc:  Designated or member state=GB     Event publication date=1990-06-22  Event code=EP/PGFP  Event indicator=Pos  Event type=Event indicating In Force  Event type=Payment or non-payment notifications  Postgrant: annual fees paid to national office   Annual fees payment date=1990-06-22     Year of payment of annual fees=12  Corresponding cc:  Designated or member state=GB     Event publication date=1991-06-29  Event code=EP/PG25  Event indicator=Neg  Event type=Event indicating Not In Force  Event type=Payment or non-payment notifications  Lapsed in a contracting state announced via postgrant inform. from nat. office to EPO Corresponding cc:  Designated or member state=GB   Effective date of the event=1991-06-29     Event publication date=1992-02-26  Event code=EP/GBPC  Event indicator=Neg  Event type=Event indicating Not In Force  Event type=Payment or non-payment notifications  GB: European patent ceased through non-payment of renewal fee Corresponding cc:  Designated or member state=GB  MEMBER STATE LEGAL DETAILS FOR NL  Actual or expected expiration date=1992-01-01    Legal state=DEAD    Status=LAPSED   Corresponding cc:  Designated or member state=NL     Event publication date=1990-06-30  Event code=EP/PGFP  Event indicator=Pos  Event type=Event indicating In Force  Event type=Payment or non-payment notifications  Postgrant: annual fees paid to national office   Annual fees payment date=1990-06-30     Year of payment of annual fees=12  Corresponding cc:  Designated or member state=NL     Event publication date=1992-01-01  Event code=EP/PG25  Event indicator=Neg  Event type=Event indicating Not In Force  Event type=Payment or non-payment notifications  Lapsed in a contracting state announced via postgrant inform. from nat. office to EPO Corresponding cc:  Designated or member state=NL   Effective date of the event=1992-01-01     Event publication date=1992-02-17  Event code=EP/NLV4  Event indicator=Neg  Event type=Event indicating Not In Force  Event type=Payment or non-payment notifications  NL: Lapsed or anulled due to non-payment of the annual fee NL: Vervallen wegens niet betalen van een jaarcijns Corresponding cc:  Designated or member state=NL
专利类型码
A1B1
国别省市代码
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