Acetone → (4-Fluorooxan-4-yl)methanol

2-(4-Fluorotetrahydro-2H-pyran-4-yl)-2-hydroxyacetonitrile (2.06 g, 12.9 mmol) was dissolved in tert-butanol (20 mL) and water (5.0 mL). To this, sodium borohydride (537 mg, 14.2 mmol) was added and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, ice and acetone were added and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated off under reduced pressure, brine was added to the residue, and extraction with chloroform was performed, followed by drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7) to give 4-fluorotetrahydro-2H-pyran-4-ylmethanol (1.59 g, yield: 92%).

1. stirringthe mixture was stirred at room temperature for 1 hour
2. customThe solvent was evaporated off under reduced pressure, brine
3. additionwas added to the residue, and extraction with chloroform
4. dry with materialby drying over anhydrous sodium sulfate
5. customThe solvent was evaporated off under reduced pressure
6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7)

ORD record

ord-d5c5154db5dc48d7bafd7666c36f86cd

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673908B2