反应详情

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%).

1. additionThe flask was then charged with air
2. stirringAfter stirring at room temperature for 15 minutes
3. temperaturethe reaction was heated
4. temperatureto reflux for 1 hour
5. temperatureThe reaction was cooled to room temperature
6. extractionextracted three times with EtOAc
7. dry with materialdried over MgSO4
8. concentrationconcentrated under reduced pressure
9. customThe crude product was chromatographed (2:1 EtOAc/hexanes)