Methanol → 2-Methoxy-α-phenyl-4-pyridinemethanol

HRID 1359258Notes

Reaction equation

HRID 1359258 reaction equation
[BH4-].[Na+].[C:3]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([O:17][CH3:18])[CH:12]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CO>O>[OH:10][CH:3]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2762474(2-Methoxypyridin-4-yl)(phenyl)methanoneHCID 4311764Sodium borohydride

Product 1

HCID 181824412-Methoxy-α-phenyl-4-pyridinemethanolYield 79.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.4 g of sodium borohydride was added little by little to a mixture of 130 g of 4-benzoyl-2-methoxypyridine and 300 ml of methanol under stirring in an ice bath. After the dropwise addition was completed, the mixture was stirred at room temperature overnight. The reaction solution was added to 1 L of water and then extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and then the solvent was removed, to give 104 g of the target compound.

Workup

  1. additionAfter the dropwise addition
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-9df3edc6687f4525bd6eb57cc33161b4
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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