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US 12,103,898 B2Granted
Process for preparing diene
AssigneeFirmenich SA
InventorsDenis Jacoby, Philippe Dupau, Lucia Bonomo, Simone Chappuis, Virginie Blanchard
Life of this patent
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Abstract
The present invention relates to the field of organic synthesis and more specifically it concerns a process for preparing compound of formula (I) catalyzed by a nickel complex. The compound of formula (II) is also part of the invention.
Claims19
A process for the preparation of a compound of formula (I)
- in a form of any one of its stereoisomers or a mixture thereof and wherein the dotted line is a carbon-carbon double or a carbon-carbon triple bond and R1 represents a C1-10 hydrocarbon group, optionally comprising one or more hydroxy, C1-15 alkoxy, C2-15 alkenyloxy, C3-15 heterocycloalkyl, C6-10 aryloxy and/or C1-4 carboxylic ester groups and R2, R3, R4 and R5, independently from each other, represent a hydrogen atom, a C1-3 alkyl group or a phenyl group;
- comprising the reaction of a compound of formula (II)
- in a form of any one of its stereoisomers and wherein the dotted line, R1, R2, R3, R4 and R5 have the same meaning as defined in formula (I) and X represents a OR6 group, a OC(═O)R6 group, a OC(═O)OR6 group or a OSO2R6 group, wherein R6 is a hydrogen atom or a C1-4 alkyl group or a phenyl group;
- with a nickel catalyst.
1 more element
A process for the preparation of a compound of formula (IV)
- in a form of any one of its stereoisomers and wherein R1 represents a C1-10 hydrocarbon group, optionally substituted by one or more hydroxy, C1-15 alkoxy, C2-15 alkenyloxy, C3-15 heterocycloalkyl, C6-10 aryloxy and/or C1-4 carboxylic ester groups;
- R2, R3 and R4, independently from each other, represent a hydrogen atom, a C1-3 alkyl group or a phenyl group and Y is a hydrogen atom, a C1-3 alkyl group, or a CHR5X group wherein R5 is a hydrogen atom, a C1-3 alkyl group or a phenyl group and X represents a OR6 group, a OC(═O)R6 group, a OC(═O)OR6 group or a OSO2R6 group, wherein R6 is a hydrogen atom or a C1-4 alkyl group or a phenyl group;
- by reacting together a compound of formula
- in a form of any one of its stereoisomers and wherein R1 has the same meaning as defined in formula (IV);
- with a compound of formula
- in a form of any one of its stereoisomers and wherein X, Y, R2, R3 and R4 have the same meaning as defined in formula (IV);
- in the presence of a nickel catalyst.
4 more elements
A compound of formula
- in a form of any one of its stereoisomers and wherein the dotted line is a carbon-carbon double or a carbon-carbon triple bond;
- R1 represents a linear or branched C1-10 alkyl group, optionally substituted by one or more hydroxy, C1-15 alkoxy, C2-15 alkenyloxy, C3-15 heterocycloalkyl, C6-10 aryloxy and/or C1-4 carboxylic ester groups;
- R2, R3, R4 and R5, independently from each other, represent a hydrogen atom, a C1-3 alkyl group or a phenyl group and X represents a OR6 group, a OC(═O)R6 group, a OC(═O)OR6 group or a OSO2R6 group, wherein R6 is a hydrogen atom or a C1-4 alkyl group or a phenyl group.
Dependencies are inferred from the claim text.