Processes for producing (4e)-5-chloro-2-isopropyl-4-pentenoate and optically active form thereof
AssigneeAsahi Glass Company, Limited
InventorsToshitsugu Sakaeda, Nobuaki Mori, Hideto Kanoh
Life of this patent
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Abstract
To provide a process for producing a (4E)-5-chloro-2-isopropyl-4-pentenoate in high yield and efficiently. A compound (2) is reacted with a base in the presence of an aprotic solvent and then with (1E)-1,3-dichloro-1-propene in the same reaction vessel to obtain a compound (3), and then either of —COOR moieties in the compound (3) is replaced with a hydrogen atom in the same reaction vessel to obtain a compound (4): wherein R is a lower alkyl group or an aralkyl group.
Claims16
A process for producing a compound of the following formula (4), which comprises reacting a compound of the following formula (2) with a base (II) in the presence of an aprotic solvent (II), and then with (1E)-1,3-dichloro-1-propene in the same reaction vessel to obtain a compound of the following formula (3), and then carrying out a reaction to replace one of —COOR moieties in the compound of the following formula (3) with a hydrogen atom in the same reaction vessel:
- wherein R is a lower alkyl group or an aralkyl group.
A process for producing a compound of the following formula (4), which comprises the following steps (a′), (b′) and (c′):
- step (a′):
- a step of reacting a compound of the following formula (1) with an alkali metal alkoxide (I) of the formula M1OR1 (wherein M1 is Na or K, and R1 is a lower alkyl group) in the presence of an aprotic solvent (I) and then with an isopropyl halide to obtain a reaction product containing a compound of the following formula (2), and then distilling off the aprotic solvent (I) from the reaction product,
- step (b′):
- a step of reacting the compound of the formula (2) obtained in the step (a′) with the alkali metal alkoxide (I) in the presence of an aprotic solvent (I), and then with (1E)-1,3-dichloro-1-propene to obtain a reaction product containing a compound of the following formula (3), and then distilling off the aprotic solvent (I) from the reaction product, and
- step (c′):
- a step of carrying out a reaction to replace one of —COOR moieties in the compound of the formula (3) obtained in the step (b′) with a hydrogen atom, in the presence of an alkali metal chloride of the formula M1Cl (wherein M1 is the same as defined above)
- wherein R is a lower alkyl group or an aralkyl group.
Dependencies are inferred from the claim text.