Methanol → Methyl 3-(2-Isopropyl-4-thiazolyl)propanoate

Participants

Reaction Steps

A solution of 225 mg (1 mmol) of (E)-ethyl 3-(2-isopropyl-4-thiazolyl)-propenoate in 10 ml of freshly distilled (from calcium hydride) methanol and 1 ml of dry THF was treated with-49 mg (2 mmol) of magnesium turnings. The mixture was stirred for 20 min, during which the magnesium was consumed. The resulting solution was poured over cold aqueous HCl, basified to pH 8 with NaHCO3, extracted with ethyl acetate, dried over Na2SO4, and concentrated. Silica gel chromatography using 10% ethyl acetate in hexane provided a mixture of the desired compound and methyl 3-(2-isopropyl-4-thiazolinyl)propanoate.

Provenance & Evidence