Acetic Acid → 5-{4-[2-(2,5-Dimethyl-4-oxazolyl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione

Participants

Reaction Steps

Sodium borohydride (0.16 g) was added to a suspension of 5-{4-[2-(2,5-dimethyl-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione (1.5 g) in methanol-N,N-dimethylformamide (1:1, V.V, 40 ml) under ice-cooling. After stirring under ice-cooling for 20 minutes, the reaction solution was poured into ice-water, and the aqueous mixture was made acid with acetic acid, and the crystals which separated out were collected by filtration to give 5-{4-[2-(2,5-dimethyl-4-oxazolyl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione (1.47 g, 97.5%). Recrystallization from chloroform-ethanol afforded colorless prisms, m.p. 223°-224° C. Elemental analysis for C17H16N2O5S, Calcd.: C, 56.66; H, 4.47; N, 7.77. Found: C, 56.36; H, 4.55; N, 7.56.

Provenance & Evidence