反应详情

温度

5 °C

To a mixture of 19.7 g of 6-tert-butyl-2-(2,2-dimethylpropyl)-5-methoxy-4-phenyl-1-indanone of 93% purity (50.3 mmol), 15.0 g of NaBH4, and 200 ml of THF 100 ml of water was slowly (for ca. 10 h) added by vigorous stirring at 5° C. The resulting mixture was stirred overnight at room temperature. Further on, 500 ml of cold water was added, the resulting mixture was acidified by 12 N HCl to pH 1, and then the crude product was extracted with 3×150 ml of dichloromethane. To a solution of the residue in 300 ml of toluene 0.5 g of TsOH was added, the resulting mixture was refluxed for 15 min with Dean-Stark head, then quickly cooled to room temperature, and treated with 50 ml of 10% aqueous K2CO3 to remove acidic impurities. The organic layer was separated, the aqueous layer was extracted with 2×75 ml of dichloromethane. The combined organic extract was dried over K2CO3 and then evaporated to dryness. The product was isolated by flash-chromatography on silica gel 60 (40-64 um, 450 m3 of silica gel, eluent: hexanes-dichloromethane=4:1, vol.). Yield 17.3 g (99%) of the title product as yellowish oil.

1. custom(for ca. 10 h)
2. additionadded
3. stirringThe resulting mixture was stirred overnight at room temperature
4. extractionthe crude product was extracted with 3×150 ml of dichloromethane
5. additionTo a solution of the residue in 300 ml of toluene 0.5 g of TsOH was added
6. temperaturethe resulting mixture was refluxed for 15 min with Dean-Stark head
7. temperaturequickly cooled to room temperature
8. additiontreated with 50 ml of 10% aqueous K2CO3
9. customto remove acidic impurities
10. customThe organic layer was separated
11. extractionthe aqueous layer was extracted with 2×75 ml of dichloromethane
12. extractionThe combined organic extract
13. dry with materialwas dried over K2CO3
14. customevaporated to dryness
15. customThe product was isolated by flash-chromatography on silica gel 60 (40-64 um, 450 m3 of silica gel, eluent: hexanes-dichloromethane=4:1, vol.)