Pentanoic acid, 5-oxo-, methyl ester → HCID 13105365, compound

Participants

Reaction Conditions

Reaction Steps

1.6M Butyl lithium solution in hexane (6.7 ml) was added to a stirred suspension of the phosphonium salt (5.0 g) in dry tetrahydrofuran (50 ml) at 5° C. under nitrogen. The dark solution was cooled to -50° C. and methyl 4-formylbutyrate (1.5 g) was added dropwise. The pale solution was stirred for 30 minutes at about -60° C., allowed to warm to -10° C., poured on to ice-sodium chloride solution and extracted with ether. The extract was washed with dilute hydrochloric acid, dried and evaporated and the residue was extracted with petroleum spirit to give a mixture of (Z) and (E) esters as an oil (2.8 g). Isomerisation by the method described in (b) above gave the title compound (2.1 g), m.p. 50° C.

Provenance & Evidence