Benzyl acetate → HCID 58059648, compound

Participants

Reaction Steps

To a solution of 2-{[tert-butyl(dimethyl)silyl]oxy}-3-methylbutanoic acid (1.0 g, 4.3 mmol) in THF (14.3 mL) at 0° C. were added carbonyldiimidazole (1.05 g, 6.45 mmol). After 15 min, the mixture was allowed to warm to ambient temperature and stirred for 48 h. This solution was cooled to −78° C. and added to a solution of preformed enolate by mixing benzyl acetate (2.18 mL, 15.1 mmol) and LDA (2.0 M in THF; 7.53 mL, 15.1 mmol) in THF (15 mL) at −78° C. The mixture was stirred at −78° C. for 1 h then warmed to −10° C. for 30 min. The mixture was cooled back to −78° C. and quenched with sat. NH4Cl. The mixture was extracted with dichloromehtane (3×). The combined organic extracts was dried over MgSO4, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→75% hexanes/ethyl acetate) gave the title compound (0.43 g).

Provenance & Evidence