Water → 5-(Benzyloxy)-2-chloropyridine

HRID 1995909Notes

Reaction equation

HRID 1995909 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.[H-].[Na+].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CN(C)C=O.C(OCC)C>[Cl:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][N:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 100137175-(Benzyloxy)-2-chloropyridine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 12.9 g (0.1 mol) of 5-hydroxy-2-chloropyridine in 50 ml of dimethylformamide is added to a suspension of 4.8 g (0.1 mol) of sodium hydride (a 50% dispersion in mineral oil; washed with toluene) in 100 ml of dimethylformamide. The mixture is stirred until the evolution of hydrogen has ceased and then, after cooling with the aid of an ice-bath, 12.6 g (0.1 mol, 11.5 cc) of benzyl chloride are introduced dropwise. The mixture is heated at 60° C. for one hour, left to stand overnight and then poured into iced water, and extraction is carried out with diethyl ether. The ether phase is washed with water, dried and filtered and the filtrate is evaporated. The product, i.e. 2-chloro-5-benzyloxypyridine, is distilled. Its boiling point (0.1 mm Hg) is 135° C.

Workup

  1. washwashed with toluene) in 100 ml of dimethylformamide
  2. temperatureafter cooling with the aid of an ice-bath
  3. waitleft
  4. washThe ether phase is washed with water
  5. customdried
  6. filtrationfiltered
  7. customthe filtrate is evaporated
  8. distillationThe product, i.e. 2-chloro-5-benzyloxypyridine, is distilled
  9. customis 135° C.

Sources & evidence

ORD record
ord-f0962c906cb7475498467f229249eb2d
Source dataset
uspto-grants-1983_09
Patent number
US04406907

Reaction notes

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