Hydrochloric Acid → (Dimethyl-1,3-thiazol-5-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A 3-neck 100 mL round-bottom flask under N2 atmosphere was charged with ethyl-2,4-dimethylthiazole-5-carboxylate (1.85 g, 10 mmol ) in anhydrous CH2Cl2 (20 mL). The mixture was cooled to −78° C. 22 mL of di-isobutylaluminum hydride (1.0 M in CH2Cl2) was added dropwise via syringe. The reaction was allowed to warm to room temperature slowly and stirred for 14 h. TLC (1:1 Hexane/EtOAc) showed no starting material. The reaction was cooled to 0° C. MeOH(2 mL) and then 1 M HCl (10 mL) were slowly added. The bath was removed and the reaction stirred for 20 min. Extract with Et2O (3×10 mL). Wash the combined organic layers with brine (10 mL). Dry over MgSO4, filter and remove solvent under vacuum. Yield: 1.363 g (95%), orange oil.

Provenance & Evidence