Ethanol → Butyl (2S)-2-hydroxybutanoate

Temperature

80 °C

n-Butyl(S)-2-hydroxy-(S)-3-phenylthiobutyrate (60 mg) was dissolved in ethanol (2.0 mL). Celite (240 mg) and an ethanol solution (3.0 mL) of Raney nickel (360 mg) were sequentially added at room temperature to the solution, and the mixture was stirred at 80° C. for 10 hours. The reaction mixture was filtered through Celite, and the filtrate was added to water (20 mL), followed by extraction with diethyl ether (20 mL×3). The organic layers were combined, and the combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (methylene chloride), to thereby yield colorless oil (36 mg, 100%).

1. filtrationThe reaction mixture was filtered through Celite
2. additionthe filtrate was added to water (20 mL)
3. extractionfollowed by extraction with diethyl ether (20 mL×3)
4. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified through silica gel column chromatography (methylene chloride)

ORD record

ord-544e52dddf3e4ef5adf8e533cdd006b1

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582791B2