3-(2-Thienyl)propanoic acid → 3-(Thiophen-2-yl)propan-1-ol

Temperature

0 °C

Borane methylsulfide complex (6.4 mL, 12.8 mmol) was added to a solution of 3-(2-thienyl)propanoic acid (1.0 g, 6.4 mmol) in THF (18 mL) at 0° C. The reaction mixture was stirred at 0° C. for 2 hours and at room temperature for 3 additional hours. After cooling down to 0° C., the reaction was quenched by addition of a saturated solution of potassium carbonate (5 mL). The aqueous layer was separated and extracted with ethyl acetate (2×15 mL) and diethyl ether (2×15 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated to dryness. The title compound was obtained as a colorless oil (1.0 g, 100%).

1. temperatureAfter cooling down to 0° C.
2. customthe reaction was quenched by addition of a saturated solution of potassium carbonate (5 mL)
3. customThe aqueous layer was separated
4. extractionextracted with ethyl acetate (2×15 mL) and diethyl ether (2×15 mL)
5. dry with materialThe combined organic phases were dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated to dryness

ORD record

ord-63cc154a584f4c0dbb69321ff3330cc5

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846711B2