Hydrochloric Acid → 3-(4-hydroxybutyl)dihydrofuran-2(3H)-one

Participants

Reaction Steps

To a mixture of 3-iodo-dihydrofuran-2(3H)-one (15.0 g, 70.8 mmol) and but-3-en-1-ol (12.2 mL, 142 mmol) in water (680 mL) under an argon atmosphere was added a 1 M solution of triethylborane in EtOH (7.1 mL, 7.1 mmol). The flask was then charged with air and the reaction was stirred at room temperature for 2 hours. Solid NaHCO3 (35.7 g, 425 mmol) was added, followed by the careful addition of 50% hypophosphorous acid (39 mL, 360 mmol). After stirring at room temperature for 15 minutes, 2,2′-azobisisobutyronitrile (1.2 g, 7.1 mmol) was added and the reaction was heated to reflux for 1 hour. The reaction was cooled to room temperature, adjusted to pH=1 via the addition of 3% HCl, and then extracted three times with EtOAc. The organic layers were combined, dried over MgSO4 and concentrated under reduced pressure. The crude product was chromatographed (2:1 EtOAc/hexanes) to provide the product as a colorless oil (3.7 g, 33%).

Provenance & Evidence