Water → 2-(Ethylamino)-4-thiazoleethanol

Participants

Reaction Steps

To a stirred solution of 1.0 M LiAlH4 in THF (179 mL, 179 mmole) was added dropwise a solution of ethyl 2-acetylamino-4-thiazoleacetate (4.4 g, 17.9 mmole) in THF (50 mL). After complete addition, the reaction mixture was heated at reflux for 3 hr, then was worked up by sequential addition of H2O (0.7 mL), 10% NaOH (0.7 mL), and H2O (2.1 mL). The resulting mixture was filtered through celite® and the filtrate was concentrated. Purification by flash chromatography on silica gel (5% MeOH/CH2H2) gave the title compound (1.6 g, 53%) as an amber oil: MS (ES) m/e 173 (M+H)+.

Provenance & Evidence