Patent ID: 6452041
Filing Date: 2002-09-17
Classification: C07B,C07C

Abstract:
A process for the preparation of a compound of the formula (IV) wherein R is aryl, C3-8 cycloalkyl, C1-10 alkyl, (aryl)C1-10 alkylene, (C3-8 cycloalkyl)C1-10 alkylene, heterocyclyl, (heterocyclyl)C1-10 alkylene, (aryl)C3-8 cycloalkylene, (C3-8 cycloalkyl)arylene or (C1-10 alkylaryl)C1-10 alkylene, wherein aryl is a mono- or bicyclic partially or fully unsaturated carbocyclic ring system containing from 4 to 10 atoms, wherein aryl is a mono- or bicyclic partially or fully unsaturated carbocyclic ring system is phenyl or naphthyl, or a partially or fully unsaturated mono- or bicyclic heterocyclic moiety having up to 10 atoms in the ring system and with up to 4 hetero-atoms in the said ring system each independently selected from N, O and S, said carbocyclic ring system and heterocyclic moiety being optionally substituted by one or more substituents each independently selected from halogen, NO2, NH2, CO2R9, phenyl, C1-6 alkyl(optionally substituted by one or more halogen), and C1-6 alkoxy(optionally substituted by one or more halogen), and wherein heterocyclyl is a 3- to 8-membered mono or bicyclic saturated heterocyclic group having from 1 to 4 ring hetero-atoms each independently selected from N, O and S, optionally substituted by one or more substituents each independently selected from halogen, NO2, NH2, CO2R9, phenyl, C1-6 alkyl(optionally substituted by one or more halogen), and C1-6 alkoxy(optionally substituted by one or more halogen); R1 is C1-6 alkoxy; R2 is OH or Oâˆ’M+, wherein M+ is a metal cation is sodium, lithium, or potassium; R9 is H or C1-6 alkyl; comprising reacting an aldehyde of formula RCHO, or a protected derivative thereof selected from the group consisting of a hemiacetal or adduct thereof wherein said adduct is a bisulphite, wherein R is as defined above, with a phosphorus compound of formula (IX): or a metal carboxylate salt thereof, selected from the group consisting of a sodium, lithium or potassium carboxylate salt thereof,wherein R1 is as defined above, and wherein P is a phosphonate moiety of formula â€”P(O)(OR3)(OR4), wherein R3 and R4 are each independently selected from H, C1-6 alkyl, benzyl and phenyl (optionally substituted by one or more C1-6 alkyl), or R3 and R4 taken together are C2-5 alkylene, or P is a phosphorane moiety of formula â€”(PR5R6R7)+Xâˆ’ wherein R5, R6 and R7 are each independently selected from C1-6 alkyl and phenyl, and X is bromine, chlorine or iodine, in the presence of a sodium, lithium or potassium C1-C6 alkoxide base, in an inert solvent, and at a temperature of from âˆ’80Â° C. to 20Â° C.