Diethyl Ether → (R)-3-(3,4-diethyl-phenyl)-2-hydroxy-propionic acid

Participants

Reaction Steps

A solution of 3.2 g (47 mmol) sodium nitrite in 20 mL water was slowly added dropwise with stirring to an ice-cooled mixture of 2.0 g (7.8 mmol) (R)-2-amino-3-(3,4-diethyl-phenyl)-propionic acid in 60 mL 0.5 M H2SO4. The reaction mixture was stirred for 3 h while cooling with ice and for 3 days at RT, combined with 80 mL diethyl ether, vigorously stirred and the organic phase is separated off. The aqueous phase was again extracted with 80 mL diethyl ether, the combined organic phases were dried and evaporated down under reduced pressure. The residue was purified by chromatography on silica gel and the product fractions were evaporated down under reduced pressure.

Provenance & Evidence