Carbon Dioxide → HCID 18673000, compound

Participants

Reaction Conditions

Reaction Steps

Diisobutylaluminum hydride (1M in toluene; 15 mL, 15 mmol) was added dropwise to a solution of 2-ethyl-4-(1-methylethyl)thiazole-5-carboxylic acid ethyl ester (Example 7; 1.7 g, 7.5 mmol) in toluene (20 mL) at −78° C. The solution was stirred in a dry ice-acetone bath overnight and as the dry ice dissipated the reaction temperature rose to −10° C.. Examination of the reaction by TLC showed a mixture of starting material and product. After the reaction was again cooled to −78° C., a second portion of diisobutylaluminum hydride (1M in toluene; 15 mL, 15 mmol) was added with stirring and the cooled reaction was allowed to proceed overnight. As before, the reaction temperature rose slowly from −78° C. to −10° C. The reaction temperature was re-adjusted to −50° C., then methanol was added dropwise and the mixture was stirred for 30 min. The resulting gel was filtered through Celite® and the filter cake was washed with ethyl acetate. Evaporation of the combined filtrates in vacuo yielded 1.5 g of 2-ethyl-4-(1-methylethyl)thiazole-5-methanol (108% of theory). This material was used without further purification in a subsequent reaction.

Provenance & Evidence