Pyridine → t-Butyl 2-mesyloxypropionate

Participants

Reaction Conditions

Reaction Steps

0.35 mole of the S optical isomer of 2-mesyloxypropionic acid was dissolved in 25 ml of pyridine and 500 ml of t-butanol, and 65 g of phosphoryl chloride was added, with stirring, at -5° C. After a further 30 minutes stirring at -5° C., and a further 2 hours at 20° C., the mixture was poured into ice-water, and methylene chloride was added. The organic layer was washed successively with dilute hydrochloric acid, sodium bicarbonate, and water, and then evaporated to give a solid which was recrystalised from light petroleum ether to give (S) t-butyl 2-mesyloxypropionate.

Provenance & Evidence