Water → 4-Vinyl-2,3-dihydrobenzofuran

Temperature

0 °C

The Part C tosylate (100 g, 314 mmol) was dissolved in THF (1200 mL) in a 2000 mL three-neck round bottomed flask equipped with a mechanical stirrer, a digital thermometer, and a pressure equalizing addition funnel at room temperature. The reaction mixture was cooled to 0° C. by an ice-water bath. To this was added a solution of t-BuOK (1 M, 345.5 mL) in THF dropwise at 0° C. over a period of 110 min. The reaction mixture was warmed to ambient temperature and stirred for additional 2 hr. Water (350 mL) and EtOAc (600 mL) were added and the two layers were separated. The aqueous layer was further extracted with EtOAc (2×150 mL). The combined EtOAc layers were washed with brine (2×150 mL) dried over MgSO4 and filtered. The solvent was removed under reduced pressure to give 46 g of the title styrene in 100% yield.

1. customequipped with a mechanical stirrer
2. additionaddition funnel at room temperature
3. temperatureThe reaction mixture was warmed to ambient temperature
4. customthe two layers were separated
5. extractionThe aqueous layer was further extracted with EtOAc (2×150 mL)
6. washThe combined EtOAc layers were washed with brine (2×150 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customThe solvent was removed under reduced pressure

ORD record

ord-b59ac0ac0c7e4492bde174944df75619

Source dataset

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06160134