Benzyl Bromide → Methyl 4-[3-(3-benzyloxy-2-pyridyl)propyl)benzoate

HRID 2395078Notes

Reaction equation

HRID 2395078 reaction equation
[OH:1][C:2]1[C:3]([CH2:8][CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[K]>CN(C=O)C>[CH2:21]([O:1][C:2]1[C:3]([CH2:8][CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5462222PotassiumHCID 18974066Methyl 4-[3-(3-hydroxy-2-pyridyl)propyl]benzoate

Product 1

HCID 18974026Methyl 4-[3-(3-benzyloxy-2-pyridyl)propyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-[3-(3-hydroxy-2-pyridyl)propyl]benzoate (0.87 g, 3.2 mmol) was dissolved in DMF (5 ml) and treated with benzyl bromide (0.66 g, 3.9 mmol) and potassium carbonate (0.53 g, 3.8 mmol). The reaction was stirred at ambient temperature potassium overnight and then partitioned between EtOAc/water. The organic phase was washed well with water, dried (MgSO4) and evaporated. The residue was purified (SiO2, CH2Cl2 /EtOAc) to give methyl 4-[3-(3-benzyloxy-2-pyridyl)propyl]benzoate as a pale yellow oil.

Workup

  1. custompartitioned between EtOAc/water
  2. washThe organic phase was washed well with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified (SiO2, CH2Cl2 /EtOAc)

Sources & evidence

ORD record
ord-1943fcaaa58749f0aceed585cf4e32d3
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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