Reaktion #1859584

Reaktionsgleichung

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

Ausbeute 99.5%

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

Ausbeute 99.5%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe 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
   Sonstigeto quench
5. 5
   Sonstigethe reaction
6. 6
   SonstigeThe layers were separated
7. 7
   Extraktionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
8. 8
   WaschenThe combined organic layers were washed with saturated brine (500 mL)
9. 9
   Trocknendried over sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated under reduced pressure

Vorschrift

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.

Quelle