Acetone → 5-(Hydroxymethyl)thiophene-2-carboxylic acid

Participants

Reaction Steps

Sodium borohydride (218 mg, 5.76 mmol) was added to a solution of commercially available 5-formyl-2-thiophenecarboxylic acid (599 mg, 3.84 mmol) in methanol (19 mL), and the mixture was stiffed under nitrogen atmosphere at room temperature for 4 hours and 30 minutes. Acetone was added to the reaction mixture, and the mixture was concentrated under vacuum. 2 M hydrochloric acid and ethyl acetate were added to the residue for partition, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under vacuum and the precipitate was washed with diethyl ether and n-hexane to obtain the title compound (529 mg, 87%).

Provenance & Evidence