Sodium borohydride → HCID 13151493, compound

Participants

Reaction Steps

To a suspension of 200 g of sodium salt of α-formyl-γ-(4-fluorophenyl)-γ-butyrolactone in 1.5 liters of methanol is added slowly 70 g of sodium borohydride with stirring. The mixture is stirred at room temperature for 18 hours, and the methanol is then distilled off under reduced pressure. The residue is dissolved in 1 liter of water, and the solution is adjusted to pH 1 with concentrated sulfuric acid and heated under reflux for 1 hour. After cooling, the solution is adjusted to pH 11-12 with 40% aqueous sodium hydroxide solution, and stirred at 50° C. for 2 hours and then cooled. The reaction mixture is extracted twice with ethyl acetate. The combined extracts are washed with water and dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is distilled to give 71 g of 2-(4-fluorophenyl)-4-(hydroxymethyl)tetrahydrofuran as colorless oil, boiling at 120°-126° C. (0.06 mmHg).

Provenance & Evidence