Tetrahydrofuran → 1-(6-Chloropyridin-2-yl)ethanone

HRID 1859393Notes

Reaction equation

HRID 1859393 reaction equation
[Cl:1][C:2]1[CH:7]=CC=C(C#N)[N:3]=1.[CH3:10][Mg]I.[CH2:13]1[CH2:17][O:16][CH2:15][CH2:14]1>C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:15][CH:14]=[C:13]([C:17](=[O:16])[CH3:10])[N:3]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 1184246-Chloropyridine-2-carbonitrileHCID 178418373HCID 178418373, compound

Product 1

HCID 115791671-(6-Chloropyridin-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-chloro-6-cyanopyridine (50 g) in THF (400 ml) is cooled to −5° C. and a solution of methylmagnesium iodide in diethyl ether (3 M, 200 ml) is added. After 1 h at 0° C. the ether is destilled off and the THF-mixture is heated to 60° C. for 1 h. The THF is evaporated and the residue is treated with ice water and acidified with 2 M hydrochloric acid. The water phase is extracted with dichloromethane and after drying and evaporation of the organic phase, the residue is purified by silica-gel flash chromatography. The title compound is obtained as an oil (11.2 g).

Workup

  1. customThe THF is evaporated
  2. additionthe residue is treated with ice water
  3. extractionThe water phase is extracted with dichloromethane
  4. customafter drying
  5. customevaporation of the organic phase
  6. customthe residue is purified by silica-gel flash chromatography

Sources & evidence

ORD record
ord-e9a636cca3c340d69cd851d12531c500
Source dataset
uspto-grants-2003_03
Patent number
US06528456B2

Reaction notes

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