Process for the preparation of substituted...

Details Process for the preparation of substituted... Process for the preparation of substituted...

C - Chemistry, Metallurgy

07

C

260/361, 260/558

C07C 43/12 (2006.01) C07C 303/22 (2006.01) C07C 309/08 (2006.01) C07C 323/22 (2006.01) C07D 307/20 (2006.01)

Patent

CA 2009008

PS/5-17442/= Process for the preparation of substituted cyclopropanecarbaldehydes Abstract The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula Image (I) in which R1 is C1-C4alkyl or benzyl, which comprises a) reacting a tetrahydrofuran of formula Image (II) in which X is halogen and R2 is unsubstituted or halo-substituted C1-C10alkyl, C3-C6- cycloalkyl that is unsubstituted or substituted by halogen, C1-C4alkyl or by C1-C4alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C1-C4alkyl, C1-C4alkoxy, nitro or cyano, with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula Image (III) in which X is halogen and R2 is unsubstituted or halo-substituted C1-C10alkyl, C3-C6cycloalkyl that is unsubstituted or substituted by halogen, C1-C4alkyl or by C1-C4alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C1-C4alkyl, C1-C4alkoxy, nitro or cyano, and b) then reacting the compound of formula III with an aqueous bisulfite solution to form a bisulfite adduct of formula Image (IV) in which X is halogen and Y is a cation equivalent of an alkali metal or alkaline earth metal ion, and c) then cyclising the adduct, in the presence of a base, with a thiolate of formula R1-S/.THETA. Z? (V) in which R1 is C1-C4alkyl or benzyl and Z is a cation equivalent of an alkali metal or alkaline earth metal ion, to form a cyclopropanecarbaldehyde of formula I, and to the individual Process Steps a), b) and c) and the combinations thereof a) + b) and b) + c), and to the novel intermediates of formulae III and IV.

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