tert-Butyl acetate → t-Butyl (S)-5-benzyloxy-3-oxononanoate

Participants

Reaction Conditions

Reaction Steps

A solution of 48.7 g of t-butyl acetate in 50 ml of dried THF was then added dropwise to the solution from a dropping funnel at the same temperature over 30 minutes, followed by stirring for 45 minutes. The resulting reaction mixture was further cooled to -50° C., and a solution of 45.4 g of methyl (S)-3-benzyloxyheptanoate in 50 ml of dried THF was added thereto over 30 minutes, followed by stirring for 2 hours while maintaining at that temperature. The reaction mixture was poured into a saturated ammonium chloride aqueous solution and extracted with diethyl ether. The extract was washed with a sodium chloride aqueous solution, and the solvent was removed by distillation under reduced pressure to obtain 67 g of a crude product, which was then purified by silica gel column chromatography to obtain 36 g (53.3%) of the titled compound.

Provenance & Evidence