4-Thiazolecarboxylic acid, 2-propyl-, ethyl ester → 4-Thiazolemethanol, 2-propyl-

Participants

Reaction Steps

A mixture of the compound from step 27c (1.2 g (6 mmol) and NaBH4 (490 mg, 13 mmol) in 15 mL of ethanol was stirred at reflux for 16 hours, then cooled and quenched with water. The mixture was extracted with ether, and the ether extract was washed with water and brine and dried over MgSO4. The solvent was removed under vacuum to give 0.72 g (76% yield) of the title compound. MS: 156(M+H)+, 173(M+NH4)30 . NMR (CDCl3) ,δ:7.04 (t, J=0.5 Hz, 1H), 4.74 (dd, J=0.5, 6 Hz, 2H), 2.96 (t, J=8 Hz, 2H), 2.70 (t, J=6 Hz, 1H), 1.82 (sx, J=8 Hz, 2H), 1.03 (t, J=8 Hz, 3H).

Provenance & Evidence