Pyridine → Chloromethyl isopropyl carbonate

Participants

Reaction Conditions

Reaction Steps

Propan-2-ol (785 mg, 13.19 mmol) was added to a solution of chloromethyl chloroformate (1.7 g, 13.19 mmol) in dry ethyl ether (20 mL). The reaction mixture was cooled to 0° C. Pyridine (1.043 g, 13.19 mmol) was added dropwise with stirring. Thereafter, the reaction mixture was stirred at room temperature for 20 hours. The heterogenous mixture was filtered and the filtrate was washed with citric acid 1% (2×20 mL), NaHCO3 1% (2×20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered and evaporated to give desired compound (1.71 g, 85%). 1H NMR (CDCl3) δ: 5.69 (s, 2H, ClCH2O), 4.92 (sept, J=6.26 Hz, 1H, OCH(CH3)2), 1.30 (d, J=6.27 Hz, 6H, OCH(CH3)2). 13C NMR (CDCl3) δ: 152.68, 73.60, 71.95, 21.52 (2C).

Provenance & Evidence