Diethyl Ether → 2-Chloromethyl-6-phenoxypyridine

HRID 414495Notes

Reaction equation

HRID 414495 reaction equation
C(N(CC)CC)C.O[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:11]=1.C1(C)C=CC(S([Cl:32])(=O)=O)=CC=1.C(OCC)C>CN(C)C1C=CN=CC=1.ClCCl>[Cl:32][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:11]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 128791556-Phenoxy-2-pyridinemethanol

Product 1

HCID 138492412-Chloromethyl-6-phenoxypyridineYield 62.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

Triethylamine (2.27 cm3) was added portionwise to a stirred solution of 2-hydroxymethyl-6-phenoxypyridine (3 g), para-toluenesulphonyl chloride (3.7 g), and 4-dimethylaminopyridine (1.17 g) in dichloromethane (30 cm3), whilst the reaction mixture was maintained at the ambient temperature (ca. 22° C.) under an atmosphere of nitrogen. After a period of four hours, the reaction mixture was poured into diethyl ether, and washed sequentially with saturated aqueous sodium bicarbonate, water and brine. The organic layer was then dried, and after removal of the solvent by evaporation under reduced pressure, the crude product was subjected to column chromatography on silica gel using dichloromethane as eluent to give 2-chloromethyl-6-phenoxypyridine (2.05 g).

Workup

  1. washwashed sequentially with saturated aqueous sodium bicarbonate, water and brine
  2. customThe organic layer was then dried
  3. customafter removal of the solvent
  4. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-a92e87a32c644371bcfac954cf101d54
Source dataset
uspto-grants-1988_12
Patent number
US04792563

Reaction notes

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