反应详情

To a suspension of magnesium (2.9 g) in THF (100 ml) was added bromocyclopropane (14.4 g, 11.9 mmol) dropwise at 0° C. under argon atmosphere. The mixture was stirred for 30 minutes at room temperature and then a solution of 7-methoxy-1-tetralone (15 g, 85.1 mmol) in THF (50 ml) was added. The mixture was refluxed for 2 hours and then cooled. Saturated aqueous ammonium chloride was introduced and the product was extracted with ethyl acetate. The extract was washed with brine and water, dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in acetic acid (100 ml) and 20% hydrobromic acid (75 ml) was added. The mixture was stirred for 15 hours at room temperature and then concentrated. To the residue was added saturated aqueous sodium hydrogen bicarbonate and the product was extracted with ethyl acetate. The extract was washed with brine and water, dried over anhydrous magnesium sulfate, and the solvent removed in vacuo. The residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:9) to afford the titled compound (20 g, yield 84%, oil).

1. temperatureThe mixture was refluxed for 2 hours
2. temperaturecooled
3. extractionthe product was extracted with ethyl acetate
4. washThe extract was washed with brine and water
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was removed in vacuo
7. dissolutionThe residue was dissolved in acetic acid (100 ml)
8. addition20% hydrobromic acid (75 ml) was added
9. stirringThe mixture was stirred for 15 hours at room temperature
10. concentrationconcentrated
11. additionTo the residue was added saturated aqueous sodium hydrogen bicarbonate
12. extractionthe product was extracted with ethyl acetate
13. washThe extract was washed with brine and water
14. dry with materialdried over anhydrous magnesium sulfate
15. customthe solvent removed in vacuo
16. customThe residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:9)