Acetyl chloride → Acetate

Participants

Reaction Steps

To a solution of butyne-1,4-diol (5 g, 58 mmol) in dry THF at room temperature (RT) was added portion-wise sodium hydride (60% dispersion in oil, 2.32 g, 58 mmol). After 4.3 hr, acetyl chloride (4.12 mL, 58 mmol) was added. After stirring at RT for 22 hr, the mixture was concentrated under reduced pressure. The residue was concentrated twice from toluene before purification on silica gel using ethyl acetate/dichloromethane (1:3) as eluent to give 2-Butyne-1,4-diol, monoacetate as an oil in 49% yield. 1H NMR (DMSO-d6) δ 5.23 (1H, bs), 4.70 (2H, t, J=1.8 Hz), 4.09 (2H, s), 2.03 (3H, s).

Provenance & Evidence