反应详情

To a solution of 9.0 g (25.7 mmol) of 6-tert-butyl-2-isobutyl-5-methoxy-4-phenylindan-1-one in 100 ml of THF and 50 ml of methanol 10.0 g (0.265 mol) of NaBH4 was added by small portions by vigorous stirring for ca. 1.5 h at room temperature. This mixture was additionally stirred overnight and then acidified by 2 M HCl to pH 1. The product was extracted with 3×150 ml of dichloromethane. The organic extract was evaporated to dryness, and a mixture of the residue with 150 ml of toluene and 0.5 g of TsOH was refluxed for 15 min using Dean-Stark head. The obtained solution was washed by 10% aqueous K2CO3. The organic layer was separated, and the aqueous layer was extracted with 2×50 ml of dichloromethane. The combined organic extract was dried over K2CO3, evaporated to dryness, and then passed through short layer of silica gel 60 (40-63 um). The silica gel layer was additionally washed by hexanes-dichloromethane (1:1, vol.). The elute was evaporated to dryness, and the residue was dried in vacuum. This procedure gave 8.52 g (99%) of yellowish oil of the title product which was further used without an additional purification.

1. waitThis mixture was additionally stirred overnight
2. extractionThe product was extracted with 3×150 ml of dichloromethane
3. extractionThe organic extract
4. customwas evaporated to dryness
5. additiona mixture of the residue with 150 ml of toluene and 0.5 g of TsOH
6. temperaturewas refluxed for 15 min
7. washThe obtained solution was washed by 10% aqueous K2CO3
8. customThe organic layer was separated
9. extractionthe aqueous layer was extracted with 2×50 ml of dichloromethane
10. extractionThe combined organic extract
11. dry with materialwas dried over K2CO3
12. customevaporated to dryness
13. washThe silica gel layer was additionally washed by hexanes-dichloromethane (1:1, vol.)
14. customThe elute was evaporated to dryness
15. customthe residue was dried in vacuum