Sodium borohydride → (4-Fluorooxan-4-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Dissolve (4-fluorotetrahydropyran-4-yl)-hydroxyacetonitrile (4.4 g, 29.8 mmol) in 2-propanol (48 mL) and water (12 mL). Cool to 0° C. under a nitrogen atmosphere. Add sodium borohydride (1.2 g, 31.7 mmol) and allow the resulting mixture to slowly warm to room temperature over 5.5 hours. Quench with acetone and stir for 1 h. Concentrate the mixture to ⅓ volume and dilute with ethyl acetate. Wash the resulting organic solution with saturated aqueous sodium bicarbonate solution and saturated aqueous ammonium chloride solution (twice). Combine the aqueous washes and dilute with saturated aqueous sodium chloride solution and extract with ethyl acetate (twice). Add these extracts to the crude reaction mixture and wash the resulting solution with saturated aqueous sodium chloride solution, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 1:1 ethyl acetate:hexanes) to give the desired compound as a yellow oil (740 mg, 18%).

Provenance & Evidence