反应详情

To a solution of 4-hydroxy-3-isopropenyl-5-nitrobenzonitrile (4.135 g, 20.25 mmol) in ethyl acetate (100 ml) was added 1.2 g of Pd/C. The resulting mixture was degassed and flushed with nitrogen, and then degassed and flushed with hydrogen using a double balloon. The reaction was stirred under hydrogen for 14 h, and then diluted with ethyl acetate, filtered through a pad of Celite and concentrated. The residue was purified by flash column chromatography using a Horizon Biotage, 65i Si column, eluting with 1 column volume of dichloromethane, followed by a linear gradient of ethyl acetate in dichloromethane from 0% to 50% over 10 column volume. It was then repurified by flash column chromatography using a Horizon Biotage, 65i Si column, eluting with 1 column volume of 5% ethyl acetate in hexanes, followed by a linear gradient of ethyl acetate in hexanes from 5% to 100% over 10 column volumes to afford the title compound. Mass spectrum (ESI) 177.4 (M+1).

1. customThe resulting mixture was degassed
2. customflushed with nitrogen
3. customdegassed
4. customflushed with hydrogen using a double balloon
5. additiondiluted with ethyl acetate
6. filtrationfiltered through a pad of Celite
7. concentrationconcentrated
8. customThe residue was purified by flash column chromatography
9. washeluting with 1 column volume of dichloromethane
10. customIt was then repurified by flash column chromatography
11. washeluting with 1 column volume of 5% ethyl acetate in hexanes