Triphenylphosphine → (S)-2-ethoxy-3-(4-{2-[4-(phenylsulfanyl)phenyl]ethoxy}phenyl)propanoic acid ethyl ester

Participants

Reaction Steps

2-[4-(Phenylsulfanyl)phenyl]-1-ethanol (1.22 g; 5.12 mmole), triphenylphosphine (2 g; 7.6 mmole) and 1,1′-(azodicarbonyl)dipiperidine were dissolved in dichloromethane (15 ml). After 10 minutes a solution of (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid (described in Example 40b) in dichloromethane (15 ml) was added and the reaction mixture was stirred over night at room temperature. The solid material was filtered off and the solvent evaporated. Chromatography of the residue on siliga gel using ethyl acetate:petroleum ether (40-60° C.), (1:99, 5:95 and 10:90) gave 1.24 g (yield 47%) of (S)-2-ethoxy-3-(4-{2-[4-(phenylsulfanyl)phenyl]ethoxy}phenyl)propanoic acid ethyl ester.

Provenance & Evidence