Methanol → HCID 70855386, compound

Participants

Reaction Steps

Acetyl chloride (0.35 mL, 4.96 mmol) was added to anhydrous methanol (3 mL) at 0° C. under nitrogen atmosphere. The mixture was stirred for 20 minutes before adding 2-[5-(3,4-dihydro-2H-1-benzopyran-6-yl)-1,3-dimethyl-1H-pyrazol-4-yl]-2-[(trimethylsilyl)oxy]acetonitrile (27b) (147 mg, 0.41 mmol). The mixture was stirred at room temperature for 1 hour then at 50-60° C. for 5 hours. The solution was concentrated in vacuo. A saturated solution of sodium hydrogencarbonate (10 mL) was added to the residue. The aqueous layer was extracted with ethyl acetate (2×10 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate 40/60) to provide the desired hydroxyl-ester (27c) (72 mg, 0.227 mmol, 55%) as a colorless oil.

Provenance & Evidence