Sodium borohydride → HCID 23157458, compound

Temperature

0 °C

To a solution of 4′-[(2-ethoxyethyl)thio]-2′,6′-dimethylbiphenyl-3-carbaldehyde (0.97 g, 3.10 mmol) in a mixture of tetrahydrofuran (4 mL) and methanol (2 mL) was added sodium borohydride (0.07 g, 1.59 mmol) under stirring at 0° C., and the mixture was stirred at the same temperature for 10 min. The reaction solution was concentrated under reduced pressure, the residue was diluted with ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=5/1) to give the title compound (0.94 g, yield 96%) as a colorless oil.

1. stirringthe mixture was stirred at the same temperature for 10 min
2. concentrationThe reaction solution was concentrated under reduced pressure
3. additionthe residue was diluted with ammonium chloride solution
4. extractionthe mixture was extracted with ethyl acetate
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=5/1)

ORD record

ord-3a48c7c5415343c186a99284bba8374a

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07786165B2