3-Chloro-2,2-dimethylpropanoyl chloride → Tert-butyl 3-chloropivaloate

Participants

Reaction Steps

A slurry of sodium tert-butoxide (195.3 g, 2.03 mol) in 800 mL of dry toluene was cooled to 0° C. in an ice bath. To the stirred slurry was added 3-chloropivaloyl chloride (XIII) (300.0 g 1.94 mol) dropwise at a rate sufficient to maintain the reaction temperature below 10° C. After the addition was complete, the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with water, the mixture extracted with ether, and the ether layer washed with water and saturated NaHCO3. After drying over MgSO4, the solution was filtered and concentrated to give the product as an amber oil. 1H NMR (CDCl3) δ 1.24 (s,6H), 1.46 (s,9H), 3.57 (s,2H); 13C NMR (CDCl3) δ 22.96, 27.70, 44.80, 53.32, 80.87, 174.5.

Provenance & Evidence