Triphenylphosphine → Methyl (R)-(+)-3-(Acetylthio)-2-methylpropionate

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-( +)-3-hydroxy-2-methylpropionic acid methyl ester (8.00 g) and triphenyl phosphin (26.64 g) in tetrahydrofuran (170 ml) was added azodicarboxylic acid diethyl ester (16 ml) was added, followed by stirring at 0° C. for 30 minutes. After addition of thioacetic acid at 0° C., the reaction mixture was stirred at room temperature for 16 hours, after which saturated aqueous solution of sodium hydrogen carbonate was added and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting residue was washed with hexane and the flitrate was concentrated. The resulting residue was distilled (83-87° C./0.2 mmHg) to yield the title compound (4.95 g, yield 41%) as a colorless oily substance.

Provenance & Evidence