Acetic Anhydride → HCID 59138690, compound

Participants

Reaction Steps

To a stirred solution of (6-chloropyridin-3-yl)(phenyl)methanol (1.5 g, 6.8 mmol), diisopropylethylamine (2.5 mL, 15 mmol), 4-dimethylaminopyridine (86 mg, 0.7 mmol) in anhydrous dichloromethane (4 mL) was added acetic anhydride (1.4 mL, 15 mmol) dropwise at 0° C. under argon. After the reaction mixture was stirred at room temperature for 2 hours, water (1 mL) and then saturated aqueous sodium bicarbonate solution (20 mL) were added slowly to quench the reaction. The mixture was stirred at room temperature for 30 minutes and then extracted with dichloromethane (3×10 mL). The combined dichlormethane extracts were dried (Na2SO4) and concentrated. Silica gel flash chromatography (0-100% ethyl acetate in hexanes) gave (6-chloropyridin-3-yl)(phenyl)methyl acetate (1.7 g, 6.5 mmol, 96% yield) as a colorless liquid. MS found: (M+H)+=262.13.

Provenance & Evidence