反应详情

A mixture of 5-bromo-1-indanone (13.0 g, 61.8 mmol), p-toluenesulfonic acid (23 mg, 0.12 mmol) and ethylene glycol (27.6 mL, 494.6 mmol) in benzene (140 mL) was refluxed for about 24 hours, using a Dean-Stark trap to remove water. The mixture was cooled, poured into excess 5% aqueous sodium bicarbonate and was extracted with toluene. The combined organic extracts were washed with brine, dried with MgSO4, filtered, and evaporated in vacuum. The residue was purified by flash column chromatography using dichloromethane as the mobile phase to give the above intermediate. MS (DCI/NH3): m/z 254, 256 (M)+.

1. temperaturewas refluxed for about 24 hours
2. customto remove water
3. temperatureThe mixture was cooled
4. additionpoured into excess 5% aqueous sodium bicarbonate
5. extractionwas extracted with toluene
6. washThe combined organic extracts were washed with brine
7. dry with materialdried with MgSO4
8. filtrationfiltered
9. customevaporated in vacuum
10. customThe residue was purified by flash column chromatography
11. customto give the above intermediate