Acetic Acid → Methyl 2-[5-(hydroxymethyl)-2-thienyl]acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(5-formyl-2-thienyl)acetate (3.88 g, 21.1 mmol) in methanol (4 mL) and tetrahydrofuran (16 mL) was added sodium borohydride (399 mg, 10.5 mmol) at −10° C. The reaction mixture was stirred at 0° C. for 1 h. Sodium borohydride (399 mg, 10.5 mmol) was added and the mixture left to stir at 0° C. for 2 h. Acetic acid (1.2 mL) was added and the reaction solution concentrated in vacuo. The residue was diluted with water (30 mL) and extracted with ethyl acetate (3×30 mL). The combined organic phases were washed with brine (20 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with 0-30% ethyl acetate in iso-hexane to give the title compound as a yellow oil (1.1 g, 28%).

Provenance & Evidence