Sodium borohydride → HCID 21547078, compound

HRID 1605652Notes

Reaction equation

HRID 1605652 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9](=[O:11])[CH3:10])=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[C:1]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][C:4](/[CH:7]=[CH:8]/[CH:9]([OH:11])[CH3:10])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 5792363(E)-4-(1,1'-Biphenyl)-4-yl-2-buten-2-one

Product 1

HCID 21547078HCID 21547078, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

22.2 Gm (0.1 mol) of (E)-4-(4-biphenylyl)-3-butene-2-one, dissolved in 1 liter of 95% ethanol, were added in small amounts within 10 minutes to a solution of 1.9 gm (0.05 mol) of sodium borohydride in 300 ml of 95% ethanol. Subsequently, the mixture was stirred for 1 hour at room temperature. The excess reducing agent was removed by careful addition of 3 gm of glacial acetic acid. The solvent was subsequently distilled off in water aspirator vacuum. 500 Ml of water were added to the residue, and the reaction mixture was exhaustively extracted with ether. The combined ether extracts were washed with water, dried over sodium sulfate and evaporated. The residue was recrystallized from ethyl acetate/petroleum ether (ratio of volume: 1:9) in the presence of charcoal. 16.1 Gm (72% of theory) of colorless crystals, m. p. 138°-139°C, were obtained; the compounds was completely identical with that prepared in Example 25 according to thin-layer chromatogram, melting point, mixed melting point and spectra.

Workup

  1. customwas removed by careful addition of 3 gm of glacial acetic acid
  2. distillationThe solvent was subsequently distilled off in water
  3. addition500 Ml of water were added to the residue
  4. extractionthe reaction mixture was exhaustively extracted with ether
  5. washThe combined ether extracts were washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was recrystallized from ethyl acetate/petroleum ether (ratio of volume: 1:9) in the presence of charcoal
  9. custom16.1 Gm (72% of theory) of colorless crystals, m. p. 138°-139°C, were obtained
  10. customthat prepared in Example 25 according to thin-layer chromatogram
  11. additionmixed

Sources & evidence

ORD record
ord-6e0b781410ac4522bed8c50345ce6d50
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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