Reaction #1379920

Reaction equation

5-bromo-1-indanone

sodium borohydride

→

5-Bromoindan-1-ol

Solvents

methanol

Conditions

Workup

1. 1
   Otherthe reaction temperature below 40° C
2. 2
   OtherThe water bath was removed
3. 3
   Otherquenched by the addition of 100 mL of water
4. 4
   OtherThe methanol was removed in vacuo
5. 5
   Otherthe residue partitioned between water and ethyl acetate
6. 6
   ExtractionThe aqueous phase was extracted with two portions of ethyl acetate
7. 7
   WashThe combined organic phases were washed with saturated aqueous sodium chloride solution
8. 8
   Dryingdried over sodium sulfate
9. 9
   Concentrationconcentrated
10. 10
    Otherto give a yellow solid which
11. 11
    Otherwas used without further purification

Procedure

To a suspension of 40 g (184 mmol) of 5-bromo-1-indanone in 500 mL of methanol in a water bath was added 16.2 g of sodium borohydride portionwise, keeping the reaction temperature below 40° C. The water bath was removed and the reaction mixture stirred at ambient temperature for 2 h and then quenched by the addition of 100 mL of water. The methanol was removed in vacuo, and the residue partitioned between water and ethyl acetate. The aqueous phase was extracted with two portions of ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated to give a yellow solid which was used without further purification. Mass spectrum (MS): m/z 195, 197 (M+1-H2O), 116 (M+1-H2O-HBr).

Source