Methanol → Methyl 5-(hydroxymethyl)thiophene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(hydroxymethyl)thiophene-2-carboxylic acid (1.430 g, 9.040 mmol) in anhydrous methanol (140 ml) concentrated sulfuric acid (88.7 mg, 0.904 mmol) was added, and the mixture was heated under reflux for 40 hrs. After cooling to 0° C., sodium carbonate (300 mg) was added, and the mixture was concentrated to about 50 ml under reduced pressure. Saturated brine was added, and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was washed with saturated aqueous ammonium chloride solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give methyl 5-(hydroxymethyl)thiophene-2-carboxylate (1.444 g, yield 92.7%) as a yellow oil.

Provenance & Evidence