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US 2025/0034074 A1Published application
Process for preparing a cyclic diene
OwnerDenis Jacoby, Simone Chappuis +1inventors
InventorsDenis Jacoby, Simone Chappuis, Fabrice Keller
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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) comprising the reaction of a compound of the formula (II) with a base having a boiling point superior to the boiling point of the compound of formula (I). Moreover, the compound of formula (I) and the compound of formula (II) are also part of the invention.
Claims20
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 n is an integer comprised between 0 and 13;
- R1, R2, R3, R4 and R5, independently from each other, represent a hydrogen atom, a C1-6 alkyl group or a C2-6 alkenyl group;
- or R4 and R5 are taken together with the atom to which they are connected to form a C3-6 cycloalkyl group;
- X is a C(O)R6, COOR6, CN or C═NR6 group wherein R6 represents a hydrogen atom, a C1-6 alkyl group or a C2-6 alkenyl group;
- comprising the reaction of a compound of the formula (II)
- in a form of any one of its stereoisomers and wherein n, X, R1, R2, R3, R4 and R5 have the same meaning as defined in formula (I) and R7 represents a hydrogen atom, a C2-6 alkenyl group, a C1-6 alkyl group optionally substituted by one or more of a halogen atom or a C6-10 aryl group optionally substituted by one or more of a hydroxy, C1-6 alkyl, C2-6 alkenyl, C1-6 alkoxy group and a halogen atom;
- with a base having a boiling point superior to the boiling point of the compound of formula (I).
4 more elements
A compound of formula (II″)
- in a form of any one of its stereoisomers and wherein R1, R2, R3, R4 and R5, independently from each other, represent a hydrogen atom, a C1-6 alkyl group or a C2-6 alkenyl group;
- or R4 and R5 are taken together with the atom to which they are attached to form a C3-6 cycloalkyl group;
- X is a C(O)R6, COOR6, CN or C═NR6 group wherein R6 represents a hydrogen atom, a C1-6 alkyl group or a C2-6 alkenyl group and R7 represents a hydrogen atom, a C2-6 alkenyl group, a C1-6 alkyl group optionally substituted by one or more of a halogen atom or a C6-10 aryl group optionally substituted by one or more of a hydroxy, C1-6 alkyl, C2-6 alkenyl, C1-6 alkoxy group and halogen atom;
- provided that 4-(but-2-enoyl)-3,5,5-trimethylcyclohex-2-en-1-yl acetate and ethyl 4-acetoxy-2,6,6-trimethylcyclohex-2-ene-1-carboxylate are excluded.
1 more element
A compound of formula (I″)
- in a form of any one of its stereoisomers or a mixture thereof and wherein R1, R2, R3, R4 and R5, independently from each other, represent a hydrogen atom, a C1-6 alkyl group or a C2-6 alkenyl group;
- or R4 and R5 are taken together with the atom to which they are attached to form a C3-6 cycloalkyl group;
- X is a C(O)R6, COOR6, CN or C═NR6 group wherein R6 represents a hydrogen atom, a C1-6 alkyl group or a C2-6 alkenyl group;
- provided that ethyl 2-ethyl-6,6-dimethylcyclohexa-1,3-diene-1-carboxylate, methyl 2,6,6-trimethylcyclohexa-1,3-diene-1-carboxylate, ethyl 2,6,6-trimethylcyclohexa-1,3-diene-1-carboxylate, 1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)ethan-1-one and 1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one are excluded.
1 more element
Dependencies are inferred from the claim text.