Tetrahydrofuran → [4-(Phenylsulfonyl)phenyl]methanol

Participants

Reaction Steps

Sodium borohydride (777 mg, 20.5 mmol) was added slowly in portions to a 0° C. solution of 4-(benzenesulfonyl)-benzaldehyde (4.29 g, 18.6 mmol) and tetrahydrofuran (60 mL). The reaction mixture was allowed to warm to room temperature, then stirred at room temperature for 4 hours. The reaction mixture was then cooled over an ice-water bath, diluted with ethyl acetate (80 mL), then carefully quenched with a saturated aqueous solution of ammonium chloride (10 mL). The mixture was washed with water (80 mL), then the organic phase was dried over MgSO4, filtered, and concentrated to afford 2.83 g (61%) of (4-benzenesulfonyl-phenyl)-methanol as a white solid. This product was used in subsequent steps without further purification.

Provenance & Evidence