Pyridine → Tert-butyl 1-chloroethyl carbonate

Temperature

-78 °C

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).

1. temperatureto warm to room temperature
2. customThe r×n was evaporated
3. dissolutiondissolved in ethyl acetate
4. washwashed with water and brine
5. dry with materialdried over magnesium sulfate
6. customevaporated
7. customevaporated under high vacuum
8. distillationThe product was distilled

ORD record

ord-79e4e82249ab47fabdd99773455e53ca

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859781B2