Sodium borohydride → HCID 21288484, compound

HRID 868431Notes

Reaction equation

HRID 868431 reaction equation
[C:1]([C:8]1[CH:9]=[C:10](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:12][CH:13]=1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[BH4-].[Na+]>C(O)C>[OH:7][CH:1]([C:8]1[CH:9]=[C:10](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13560734HCID 13560734, compound

Product 1

HCID 21288484HCID 21288484, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The ketone, trans-3-hexanoyl stilbene of Example 20 (1 g) was dissolved in ethanol, and sodium borohydride (0.2 g) was added. The mixture was stirred overnight. Excess of the borohydride was destroyed by carefully adding a dilute HCl solution. The aqueous solution was extracted thoroughly with ether, and then the ether extract was washed with brine and dried. On removal of all volatiles, the pure alcohol was obtained as a clear, colorless liquid in quantitative yield.

Workup

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

Sources & evidence

ORD record
ord-30b76913f71145c78c8cc230ceca733d
Source dataset
uspto-grants-1988_10
Patent number
US04778931

Reaction notes

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