반응 #1612650

반응 방정식

HCl

6-tert-butyl-2-isobutyl-5-methoxy-4-phenylindan-1-one

methanol

NaBH4

→

yellowish oil

수율 99.1%

5-tert-Butyl-2-isobutyl-6-methoxy-7-phenyl-1H-indene

수율 99.1%

용매

THF

반응 조건

후처리

1. 1
   workup.WAITThis mixture was additionally stirred overnight
2. 2
   추출The product was extracted with 3×150 ml of dichloromethane
3. 3
   추출The organic extract
4. 4
   기타was evaporated to dryness
5. 5
   workup.ADDITIONa mixture of the residue with 150 ml of toluene and 0.5 g of TsOH
6. 6
   온도was refluxed for 15 min
7. 7
   세척The obtained solution was washed by 10% aqueous K2CO3
8. 8
   기타The organic layer was separated
9. 9
   추출the aqueous layer was extracted with 2×50 ml of dichloromethane
10. 10
    추출The combined organic extract
11. 11
    건조was dried over K2CO3
12. 12
    기타evaporated to dryness
13. 13
    세척The silica gel layer was additionally washed by hexanes-dichloromethane (1:1, vol.)
14. 14
    기타The elute was evaporated to dryness
15. 15
    기타the residue was dried in vacuum

실험 절차

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.

출처