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US 8,263,797 B2Granted
Method for producing cyclopropane carboxylic acid compound and intermediate therefor
AssigneeSumitomo Chemical Company, Limited
InventorsToru Uekawa, Jun Ohshita, Kouji Yoshikawa, Ichiro Komoto
Life of this patent
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Abstract
A method for producing a cyclopropanecarboxylic acid compound represented by formula (VI) (wherein R denotes the same as below), which comprising reacting a compound represented by formula (V) (wherein R denotes a chain hydrocarbon group having 1 to 10 carbon atoms or the like, and R1 denotes a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted with a halogen atom or the like) with an alkali metal borohydride compound in the presence of a solvent.
Claims24
A method for producing a cyclopropanecarboxylic acid compound represented by formula (VI)
- (wherein R denotes the same as below),
- which comprising reacting a compound represented by formula (V)
- (wherein R denotes a chain hydrocarbon group having 1 to 10 carbon atoms which group is optionally substituted with at least one group selected from the group consisting of a halogen atom, an acyl group having 2 to 7 carbon atoms, an optionally substituted alkoxy group having 1 to 7 carbon atoms, an optionally substituted alkylthio group having 1 to 3 carbon atoms and an optionally substituted phenyl group,
- a cyclic hydrocarbon group having 3 to 10 carbon atoms, or
- a hydrogen atom, and
- R1 denotes a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted with a halogen atom or
- a phenyl group)
- with an alkali metal borohydride compound in the presence of a solvent.
5 more elements
A compound represented by formula (II)
- (wherein R denotes a chain hydrocarbon group having 1 to 10 carbon atoms which group is optionally substituted with at least one group selected from the group consisting of a halogen atom, an acyl group having 2 to 7 carbon atoms, an optionally substituted alkoxy group having 1 to 7 carbon atoms, an optionally substituted alkylthio group having 1 to 3 carbon atoms and an optionally substituted phenyl group,
- a cyclic hydrocarbon group having 3 to 10 carbon atoms, or
- a hydrogen atom).
A compound represented by formula (V)
- (wherein R denotes a chain hydrocarbon group having 1 to 10 carbon atoms which group is optionally substituted with at least one group selected from the group consisting of a halogen atom, an acyl group having 2 to 7 carbon atoms, an optionally substituted alkoxy group having 1 to 7 carbon atoms, an optionally substituted alkylthio group having 1 to 3 carbon atoms and an optionally substituted phenyl group,
- a cyclic hydrocarbon group having 3 to 10 carbon atoms or
- a hydrogen atom, and
- R1 denotes a chain hydrocarbon group having 1 to 10 carbon atoms which group is optionally substituted with a halogen atom or
- a phenyl group).
2 more elements
A method for producing a cyclopropanecarboxylic acid compound represented by formula (IX)
- (wherein R2 denotes the same as below),
- which comprises reacting a compound represented by formula (Va)
- (wherein R′ denotes a chain hydrocarbon group having 1 to 10 carbon atoms which group is optionally substituted with at least one group selected from the group consisting of a halogen atom, an acyl group having 2 to 7 carbon atoms, an optionally substituted alkoxy group having 1 to 7 carbon atoms, an optionally substituted alkylthio group having 1 to 3 carbon atoms and an optionally substituted phenyl group or
- a cyclic hydrocarbon group having 3 to 10 carbon atoms, and
- R1 denotes a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted with a halogen atom or
- a phenyl group)
- with an alkali metal borohydride compound in the presence of a solvent to obtain a cyclopropanecarboxylic acid compound represented by formula (VIa)
- (wherein R′ denotes the same as above), and
- reacting the obtained cyclopropanecarboxylic acid compound represented by formula (VIa) with a compound represented by formula (VIII)
- R2—OH (VIII)
- (wherein R2 is different from the R′ and denotes a chain hydrocarbon group having 1 to 10 carbon atoms which group is optionally substituted with at least one group selected from the group consisting of a halogen atom, an acyl group having 2 to 7 carbon atoms, an optionally substituted alkoxy group having 1 to 7 carbon atoms, an optionally substituted alkylthio group having 1 to 3 carbon atoms and an optionally substituted phenyl group, or
- a cyclic hydrocarbon group having 3 to 10 carbon atoms)
- in the presence of an alkali metal hydroxide.
10 more elements
A method for producing a cyclopropanecarboxylic acid represented by formula (VII)
- which comprises reacting a compound represented by formula (Va)
- (wherein R′ denotes the same as below)
- with an alkali metal borohydride compound in the presence of a solvent to obtain a cyclopropanecarboxylic acid compound represented by formula (VIa)
- (wherein R′ denotes a chain hydrocarbon group having 1 to 10 carbon atoms which group is optionally substituted with at least one group selected from the group consisting of a halogen atom, an acyl group having 2 to 7 carbon atoms, an optionally substituted alkoxy group having 1 to 7 carbon atoms, an optionally substituted alkylthio group having 1 to 3 carbon atoms and an optionally substituted phenyl group, or
- a cyclic hydrocarbon group having 3 to 10 carbon atoms, and
- R1 denotes a chain hydrocarbon group having 1 to 10 carbon atoms which group is optionally substituted with a halogen atom or a phenyl group), and
- hydrolyzing the obtained cyclopropanecarboxylic acid compound represented by formula (VIa).
4 more elements
A method for producing a cyclopropanecarboxylic acid compound represented by formula (IXa)
- (wherein R3 denotes the same as below),
- which comprises reacting a compound represented by formula (Vb)
- (wherein R1 denotes a chain hydrocarbon group having 1 to 10 carbon atoms which group is optionally substituted with a halogen atom or
- a phenyl group)
- with an alkali metal borohydride compound in the presence of a solvent to obtain a cyclopropanecarboxylic acid compound represented by formula (VIb)
- and
- reacting the obtained cyclopropanecarboxylic acid compound represented by formula (VIb) with a compound represented by formula (VIIIa)
- R3—OH (VIIIa)
- (wherein R3 denotes a chain hydrocarbon group having 1 to 10 carbon atoms which group is optionally substituted with at least one group selected from the group consisting of a halogen atom, an acyl group having 2 to 7 carbon atoms, an optionally substituted alkoxy group having 1 to 7 carbon atoms, an optionally substituted alkylthio group having 1 to 3 carbon atoms and an optionally substituted phenyl group, or
- a cyclic hydrocarbon group having 3 to 10 carbon atoms)
- in the presence of a zirconium compound.
8 more elements
Dependencies are inferred from the claim text.