Diethyl Ether → 2-METHOXY-6-PHENYLPYRIDINE

HRID 2117810Notes

Reaction equation

HRID 2117810 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.[Cl-].[NH4+].C(O[CH2:15][CH3:16])C>[Ni](Cl)Cl.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:9][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:16]2[CH:15]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 25517Ammonium ChlorideHCID 870092-Chloro-6-methoxypyridine

Product 1

HCID 114694882-METHOXY-6-PHENYLPYRIDINE

Reagents, catalysts & solvents 1

HCID 2724937Dichloro(1,1'-(1,3-propanediyl)bis(1,1-diphenylphosphine-kappaP))nickelCatalyst

Procedure

An ether (30 ml) solution of phenyl magnesium bromide ether solution (12.3 ml, 3.0 M, 37.0 mmol) was dropwise added to a mixture of 2-chloro-6-methoxypyridine (4.4 ml, 37.0 mmol), 1,3-bis(diphenylphosphino)propane nickel (II) chloride (228 mg) and diethyl ether (40 ml) at room temperature while 30 minutes. Thereafter, this reaction mixture was stirred under reflux for 1 hour, then the mixture was poured into an aqueous ammonium chloride solution, an organic layer was separated, furthermore an aqueous layer was extracted with dichloromethane. The organic layer was combined, and the solvent was distilled off, and the residue was filtered through a silica gel, thereby obtaining 7.0 g of crude 2-methoxy-6-phenylpyridine as pale yellow oil.

Workup

  1. temperatureunder reflux for 1 hour
  2. customan organic layer was separated
  3. extractionfurthermore an aqueous layer was extracted with dichloromethane
  4. distillationthe solvent was distilled off
  5. filtrationthe residue was filtered through a silica gel

Sources & evidence

ORD record
ord-e336daa6a6a94cf59b46c910342b2202
Source dataset
uspto-grants-2008_10
Patent number
US07442797B2

Reaction notes

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