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

Temperature

0 °C

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.

1. temperaturethe mixture was heated
2. temperatureunder reflux for 40 hrs
3. concentrationthe mixture was concentrated to about 50 ml under reduced pressure
4. additionSaturated brine was added
5. extractionthe mixture was extracted 3 times with ethyl acetate
6. washThe combined organic layer was washed with saturated aqueous ammonium chloride solution and saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure

ORD record

ord-84ec7b39bd5747a4b607f285d8417237

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999989B2