反応 #1859589

反応方程式

Sodium borohydride

compound 21

4-([1,1′-Biphenyl]-2-yl)-2-((1-methylcyclohexyl)methyl)-2,3-dihydro-1H-inden-1-one

→

crude compound 22

収率 102.1%

4-([1,1′-Biphenyl]-2-yl)-2-((1-methylcyclohexyl)methyl)-2,3-dihydro-1H-inden-1-ol

収率 102.1%

溶媒

THF

ethanol

反応条件

後処理

1. 1
   濃縮The 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.ADDITION1 M aqueous HCl was added dropwise
4. 4
   その他to quench
5. 5
   その他the reaction
6. 6
   その他The layers were separated
7. 7
   抽出the aqueous layer was extracted with ethyl acetate (2×100 mL)
8. 8
   洗浄The combined organic layers were washed with saturated brine (500 mL)
9. 9
   乾燥dried over sodium sulfate
10. 10
    ろ過filtered
11. 11
    濃縮concentrated under reduced pressure

実験手順

Sodium borohydride (0.56 g, 14.83 mmol, 1.5 equiv) was added in portions at 0° C. to a solution of compound 21 (3.9 g, 9.88 mmol, 1.0 equiv) in THF (50 mL) and ethanol (50 mL). The reaction mixture was stirred at room temperature overnight, when L/CMS 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). 1 M aqueous 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 22 (4.0 g, >99% yield) as a pale-yellow oil. This material was used subsequently.

出典