반응 #1859584

반응 방정식

Sodium borohydride

compound 13

4-(3,5-Di-tert-butylphenyl)-2-((1-methylcyclohexyl)methyl)-2,3-dihydro-1H-inden-1-one

THF

→

crude compound 14

수율 99.5%

4-(3,5-Di-tert-butylphenyl)-2-((1-methylcyclohexyl)methyl)-2,3-dihydro-1H-inden-1-ol

수율 99.5%

용매

ethanol

반응 조건

후처리

1. 1
   농축The mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONthe residue was diluted with ethyl acetate (300 mL) and water (50 mL)
3. 3
   workup.ADDITION1M HCl was added dropwise
4. 4
   기타to quench
5. 5
   기타the reaction
6. 6
   기타The layers were separated
7. 7
   추출the aqueous layer was extracted with ethyl acetate (2×100 mL)
8. 8
   세척The combined organic layers were washed with saturated brine (500 mL)
9. 9
   건조dried over sodium sulfate
10. 10
    여과filtered
11. 11
    농축concentrated under reduced pressure

실험 절차

Sodium borohydride (1.32 g, 34.83 mmol, 1.5 equiv) was added in portions at 0° C. to a solution of compound 13 (10.0 g, 23.22 mmol, 1.0 equiv), THF (100 mL) and ethanol (100 mL). The reaction mixture was stirred at room temperature overnight, when LCMS indicated that the reaction was complete. The mixture was concentrated under reduced pressure and the residue was diluted with ethyl acetate (300 mL) and water (50 mL). 1M HCl was added dropwise to quench the reaction. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with saturated brine (500 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the crude compound 14 (10.0 g, >99% yield) as a pale-yellow oil. This material was used subsequently.

출처