Tetrahydrofuran → 1-(2,3-Dimethylimidazo[2,1-b][1,3]thiazol-5-yl)-3-phenylprop-2-en-1-ol

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Reaction Steps

A solution of 2,3-Dimethyl-α-(2-phenyl-E-ethenyl)imidazo[2,1-b]thiazole-5-methanone (FIG. D-2) (0.34 g) in 1:1 ethanol:THF (40 mL) was treated with a solution of NaBH4 (0.35 g) in ethanol (5 mL). The solution was reacted for 2.5 hours, evaporated in vacuo, and the residue was diluted with water. The precipitated 2,3-Dimethyl-α-(2-phenylethenyl)imidazo[2,1-b]thiazole-5-methanol (FIG. D-5) was extracted into ethyl acetate, the extract was dried and evaporated to a viscous residue. The residue was triturated with ethyl acetate to yield 2,3-Dimethyl-α-(2-phenylethenyl)imidazo[2,1-b]thiazole-5-methanol (FIG. D-5), 0.28 g, m.p. 149-151° after crystallization from acetonitrile.

Provenance & Evidence