Benzyl Alcohol → 4-(Benzyloxy)pyridine

HRID 861379Notes

Reaction equation

HRID 861379 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1>CS(C)=O>[CH2:3]([O:10][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 122884-ChloropyridineHCID 24758Sodium hydride

Product 1

HCID 123288284-(Benzyloxy)pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of sodium hydride (80% dispersed in oil, 876 mg, 29.2 mmol) in DMSO (10 ml) was added benzyl alcohol (3 ml, 29.2 mmol) and the mixture stirred at room temperature for 1 hour. To this was added 4-chloropyridine (3.3 g, 29.2 mmol) and the reaction stirred at room temperature overnight. The precipitated sodium chloride was removed by filtration and the filtrate diluted with water (100 ml) and extracted with ether (3×120 ml). The combined organic layers were dried (MgSO4) and evaporated in vacuo to yield the title compound as an oil (4.8 g, 95%); δH (CDCl3) 5.11 (2H, s, PhCH2O), 6.87 (2H, d, J 6.3 Hz, 3-H, 5-H), 7.29-7.42 (5H, m, Ph), and 8.42 (2H, d, J 6.3 Hz, 2-H, 6-H).

Workup

  1. stirringthe reaction stirred at room temperature overnight
  2. customThe precipitated sodium chloride was removed by filtration
  3. additionthe filtrate diluted with water (100 ml)
  4. extractionextracted with ether (3×120 ml)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8e1e4b65ad164f7ea1a076a8835be972
Source dataset
uspto-grants-1998_02
Patent number
US05714498

Reaction notes

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