1-(2-Phenylquinolin-4-yl)ethanone → 1-(2-Phenylquinolin-4-yl)-ethanol

HRID 1597371Notes

Reaction equation

HRID 1597371 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]([C:17](=[O:19])[CH3:18])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([C:7]2[CH:16]=[C:15]([CH:17]([OH:19])[CH3:18])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 3441581-(2-Phenylquinolin-4-yl)ethanoneHCID 4311764Sodium borohydride

Product 1

HCID 234991661-(2-Phenylquinolin-4-yl)-ethanolYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1-(2-phenylquinolin-4-yl)-ethanone (0.233 g, 0.943 mmol) in 5 ml methanol, at room temperature sodium borohydride (0.036 g, 0.943 mmol) was added and the solution stirred for 30 minutes. The reaction mixture was concentrated and partitioned between EtOAc (10 ml) and water (5 ml). The organic layer was dried over sodium sulfate, filtered, concentrated and column purified (hexane:EtOAc; 3.5:1.5) to give 0.145 g (62%) of the product as a syrup which was used as such for the subsequent step.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between EtOAc (10 ml) and water (5 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customcolumn purified (hexane:EtOAc; 3.5:1.5)

Sources & evidence

ORD record
ord-09b020983e8b4b53a304e61dd7a7a5a8
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

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