Pyridine → Tert-butyl 1-chloroethyl carbonate

Participants

Reaction Conditions

Reaction Steps

t-Butanol (3.34 mL, 35 mmol) and pyridine (3.39 mL, 42 mmol) were dissolved in 90 mL methylene chloride and cooled to −78° C. 1-Chloroethyl chloroformate (5.0 g, 35 mmol) was added dropwise and the reaction was slowly allowed to warm to room temperature, then stirred for 3 days. The r×n was evaporated, dissolved in ethyl acetate, then washed with water and brine, dried over magnesium sulfate and evaporated. It was noted that product evaporated under high vacuum. The product was distilled to yield 1-chloroethyl t-butyl carbonate a colorless oil (2.46 g, 39% yield).). 1H NMR (400 MHz, CDCl3) δ 6.41 (d, J=5.6 Hz, 1H), 1.82 (d, J=5.6 Hz, 3H), 1.53 (s, 9H).

Provenance & Evidence