Sodium borohydride → HCID 54516678, compound

HRID 414842Notes

Reaction equation

HRID 414842 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:9]=1.[BH4-].[Na+]>C(O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([OH:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53699513HCID 53699513, compound

Product 1

HCID 54516678HCID 54516678, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The ketone of Example 20 (1 g) is dissolved in ethanol, and sodium borohydride (0.2 g) is added. The mixture is stirred at room temperature overnight. Excess of the borohydride is destroyed by carefully adding a dilute HCl solution. The aqueous solution is extracted thoroughly with ether, and then the ether extract is washed with brine and dried. On removal of all volatiles, the pure alcohol is obtained as a clear, coloreess liquid in quantitative yield.

Workup

  1. customExcess of the borohydride is destroyed
  2. additionby carefully adding a dilute HCl solution
  3. extractionThe aqueous solution is extracted thoroughly with ether
  4. extractionthe ether extract
  5. washis washed with brine
  6. customdried
  7. customOn removal of all volatiles

Sources & evidence

ORD record
ord-5003bcb62af44b79958ccd090d4e5dec
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

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