Triethylamine → Ethyl 4-butyrylbenzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of the crude alcohol (1.0 g, 4.5 mmol) in dichloromethane (16.7 mL), dimethylsulfoxide (4.79 mL) and triethylamine (2.28 g, 22.5 mmol) was cooled to 0° C. Sulfur trioxide pyridine complex (2.15 g, 13.5 mmol) was added in portions and the mixture stirred at 0° C. for 1 hour. The reaction was then allowed to warm to room temperature and stir for 2 hours. The reaction was quenched with brine and diluted with dichloromethane. The layers were separated and the aqueous was extracted again with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (0-30% ethyl acetate in heptane) gave ethyl 4-butyrylbenzoate (Intermediate 1). 1H NMR (400 MHz, CDCl3) δ 8.05-8.17 (m, 2 H), 8.04-7.92 (m, 2 H), 4.40 (q, J=7.15 Hz, 2 H), 2.96 (t, J=7.22 Hz, 2 H), 1.86-1.69 (m, 2 H), 1.40 (t, J=7.12 Hz, 3 H), 1.00 (t, J=7.22 Hz, 3 H).

Provenance & Evidence