Acetyl chloride → Ethyl (R)-4-Azido-3-Acetoxybutyrate

Participants

Reaction Conditions

Reaction Steps

In a 100 ml four-necked flask were charged 5.0 g (28.8 mmol) of ethyl (R)-4-azido-3-hydroxybutyrate, 3.5 g (34.6 mmol) of triethylamine, 0.11 g (0.900 mmol) of 4-dimethylaminopyridine and 50 ml of tetrahydrofuran, and after the mixture was cooled to 0° C., 2.50 g (31.8 mmol) of acetyl chloride was slowly added thereto dropwise in a nitrogen stream. After the addition, the reaction mixture was further stirred at room temperature overnight, and then the solvent was distilled under reduced pressure to give 4.94 g of a concentrate. The concentrate was subjected to column chromatography (ethyl acetate/hexane=1/10 by volume) to obtain 4.50 g (73%) of the title compound.

Provenance & Evidence