Sulfuryl chloride → Ethyl 2-chloro-3-oxohexanoate

Participants

Reaction Conditions

Reaction Steps

3-oxo-hexanoic acid ethyl ester (29.7 g, 188 mmol) was dissolved in Et2O (400 ml). The solution was cooled to 0° C., and sulfuryl chloride (22.6 ml, 282 mmol) was added dropwise. The solution gradually warmed to RT over 4 h. The solution was neutralized to pH 7 with a solution of aqueous saturated NaHCO3. The organic layer was separated, washed with brine, and dried over sodium sulfate. Evaporation under reduced pressure yielded 2-chloro-3-oxo-hexanoic acid ethyl ester (intermediate Id, 36 g, 100%). 1H-NMR (CDCl3, ppm): 0.95 d (3H); 1.35 d (3H); 1.58 m (2H); 2.7 t (2H); 4.28(d (2H); 4.78 s (1H).

Provenance & Evidence