Sodium borohydride → HCID 20336140, compound

HRID 1706505Notes

Reaction equation

HRID 1706505 reaction equation
[Br:1]/[CH:2]=[CH:3]/[C:4](=[O:14])[C:5]([CH3:13])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6].[BH4-].[Na+]>CO>[Br:1]/[CH:2]=[CH:3]/[CH:4]([OH:14])[C:5]([CH3:6])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20336134HCID 20336134, compound

Product 1

HCID 20336140HCID 20336140, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An ice-cold solution of 7.8 g. of 1-bromo-4-methyl-4-phenyl-trans-1-penten-3-one in 100 ml. of methanol was treated with 1.4 g. of sodium borohydride and stirred at 0° for one hour. The solvent was evaporated and the residue was dissolved in water then extracted with ether. The ether extract was dried with MgSO4 and evaporated to afford 8.0 g. of the title product as a colorless oil, λmaxfilm 2.95, 3.4, 6.12, 6.20, 6.62, 6.88, 7.18, 7.28, 7.82, 9.30, 9.68, 10.00, 10.55, 12.95, 13.45 and 14.24 μ.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water
  3. extractionthen extracted with ether
  4. extractionThe ether extract
  5. dry with materialwas dried with MgSO4
  6. customevaporated
  7. customto afford 8.0 g

Sources & evidence

ORD record
ord-77eab5f3d5a04c30b9e41080a3e9f688
Source dataset
uspto-grants-1980_06
Patent number
US04207419

Reaction notes

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