Gamma-Butyrolactone → HCID 59244973, compound

Participants

Reaction Steps

A solution of γ-butyrolactone (2 g, 23.3 mmol) in dehydrated tetrahydrofuran (250 ml) was cooled to −78° C. under a nitrogen atmosphere, and dehydrated tetrahydrofuran solution of 3-methoxybenzoyl chloride (4.17 g, 24.5 mmol) was added, followed by slow addition of lithium hexamethyldisilazide (LHMDS, 1M tetrahydrofuran solution, 46.6 ml, 46.6 mmol). After stirring for 1 hour, saturated sodium hydrogencarbonate aqueous solution (50 ml) was added at −78° C. followed by quenching. After extraction with ethyl acetate (200 ml), the organic layer was washed with brine (2×200 ml), dried over sodium sulfate, and subsequently the solvent was removed under reduced pressure, to obtain a crude product as a yellow oil. The crude was purified by silica gel column chromatography (hexane/ethyl acetate=50/50), to obtain the desired compound as a yellow solid (1.84 g, 36%).

Provenance & Evidence