Sodium borohydride → HCID 21547106, compound

HRID 1605660Notes

Reaction equation

HRID 1605660 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[C:10](=[O:12])[CH3:11])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[CH:10]([OH:12])[CH3:11])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21547086HCID 21547086, compound

Product 1

HCID 21547106HCID 21547106, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

30.0 Gm (0.117 mol) of (E)-4-(2-chloro-4-biphenylyl)-3-butene-2-one, dissolved in 150 ml of 95% ethanol, were added in small amounts within 10 minutes to a solution of 2.7 gm (0.0714 mol) of sodium borohydride in 200 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 4 gm of glacial acetic acid. The solvent was then distilled off in a water aspirator vacuum. 500 ml of water were added to the residue, and the mixture was exhaustively extracted with ether. The combined ether extracts were washed with water, dried over sodium sulfate and evaporated. The residue, a colorless viscous oil, was distilled in a high vacuum, b.p. 175°-180°C at 0.1 mm Hg. Yield: 23.0 gm (76% of theory).

Workup

  1. customwas removed by careful addition of 4 gm of glacial acetic acid
  2. distillationThe solvent was then distilled off in a water
  3. addition500 ml of water were added to the residue
  4. extractionthe 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. distillationThe residue, a colorless viscous oil, was distilled in a high vacuum, b.p. 175°-180°C at 0.1 mm Hg

Sources & evidence

ORD record
ord-eaca043a6f7a416f87a89ccd86a2894b
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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