Diethyl Ether → 2-Benzyl-6-methoxypyridine

HRID 1359264

Reaction equation

HRID 1359264 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].C(OCC)C.Br[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[N:17]=1>CC(P(C1C=CC=CC=1)C1C=CC=CC=1)C.C1C=CC(PC2C=CC=CC=2)=CC=1.[Cl-].[Ni].O1CCCC1>[CH2:1]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7498Benzyl BromideHCID 2568102-Bromo-6-methoxypyridineHCID 5462224Magnesium

Product 1

HCID 219422742-Benzyl-6-methoxypyridine

Reagents, catalysts & solvents 2

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A Grignard's reagent prepared from 123 ml of benzyl bromide, 30 g of magnesium and 400 ml of diethylether was slowly added dropwise into a mixture of 150 g of 2-bromo-6-methoxypyridine, 4.3 g of 1,3-bis(diphenylphosphino)propanenickel(II) chloride and 500 ml of tetrahydrofuran under stirring in an ice bath. After stirring overnight as it was, the mixture was extracted with an aqueous ammonium chloride solution and hexane. The organic phase was washed with water and then brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 1% and 1.5% of ethyl acetate/hexane, to give 150 g of the target compound.

Workup

  1. stirringAfter stirring overnight as it
  2. extractionthe mixture was extracted with an aqueous ammonium chloride solution and hexane
  3. washThe organic phase was washed with water
  4. dry with materialbrine, dried over anhydrous magnesium sulfate
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-3545b138c24840c7a248a5339a693d9e
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Linked notes

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