(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.
(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.
(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 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