1,2-Dimethoxyethane → Ethyl 4-(pyridin-4-yl)benzoate

HRID 278565Notes

Reaction equation

HRID 278565 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.B([O-])([O-])O[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.C(=O)([O-])O.[Na+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[N:18]1[CH:19]=[CH:20][C:15]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 22043Ethyl 4-bromobenzoateHCID 516892Sodium BicarbonateHCID 867578874-Pyridyl borate

Product 1

HCID 15294733Ethyl 4-(pyridin-4-yl)benzoateYield 56.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

To a mixture of ethyl 4-bromobenzoate (2.29 g), 4-pyridyl borate (1.23 g), 1 M sodium hydrogen carbonate solution (30 ml) and 1,2-dimethoxyethane (40 ml) was added tetrakis(triphenylphosphine)palladium (0.3 g) and the mixture was stirred for 3 hours with reflux under nitrogen atmosphere. To the mixture was added water and the solution was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography, and eluted with hexane-ethyl acetate (2:1) to give the title compound as crystals (1.15 g, 50.7%).

Workup

  1. temperaturewith reflux under nitrogen atmosphere
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washeluted with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-08186b392d05445ba3a70fe0619d71c2
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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