Pyridine → Chloromethyl isopropyl carbonate

Participants

Reaction Conditions

Reaction Steps

A solution of chloroformic acid chloromethyl ester (6.23 mL, 70.0 mmol) and isopropyl alcohol (4.4 g, 73.0 mmol) in anhydrous ether (150 mL) was added dropwise to a solution of pyridine (5.7 mL) at 0° C. The reaction mixture was stirred for 1 h at 0° C. and then 3 h at room temperature. The reaction mixture was diluted with ether and then washed successively with water, 10% hydrochloric acid and brine. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield chloromethyl isopropyl carbonate. The product was carried forward without further purification. 1H NMR (CDCl3): 5.68 (s, 2H), 4.90 (m, 1H), 1.32 ppm (d, 6H).

Provenance & Evidence