Ammonium Chloride → 2-Benzyl-6-(2-ethoxyethyl)oxypyridine

HRID 1359381

Reaction equation

HRID 1359381 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][O:20][CH2:21][CH3:22])[N:12]=1.[Cl-].[NH4+]>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:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][O:20][CH2:21][CH3:22])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 181824552-Bromo-6-(2-ethoxyethoxy)pyridineHCID 178418336HCID 178418336, compound

Product 1

HCID 181822222-Benzyl-6-(2-ethoxyethyl)oxypyridine

Reagents, catalysts & solvents 2

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.09 mol tetrahydrofuran solution containing benzylmagnesium chloride was slowly added dropwise into a mixture of 1 g of 2-bromo-6-(2-ethoxyethyl)oxypyridine, 145 mg of 1,3-bis(diphenylphosphino)propanenickel(II) chloride and 5 ml of tetrahydrofuran with stirring under ice-cooling in a nitrogen atmosphere. After stirring for 2.5 hours, an aqueous saturated ammonium chloride solution was added thereto and the mixture was extracted with ethyl acetate. The organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 5% ethyl acetate/hexane as an eluent for separation and purification, to give 1 g of the target compound.

Workup

  1. temperaturecooling in a nitrogen atmosphere
  2. stirringAfter stirring for 2.5 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was further washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed
  7. customfor separation and purification

Sources & evidence

ORD record
ord-cb6d21e19be948e0a7558a6ff7dd6523
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Linked notes

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