Réaction #1859584

Équation de réaction

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

Rendement 99.5%

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

Rendement 99.5%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   ConcentrationThe 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
   Autreto quench
5. 5
   Autrethe reaction
6. 6
   AutreThe layers were separated
7. 7
   Extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
8. 8
   LavageThe combined organic layers were washed with saturated brine (500 mL)
9. 9
   Séchagedried over sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    Concentrationconcentrated under reduced pressure

Mode opératoire

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.

Source