Benzyl Alcohol → Methyl 3-(2-benzyloxycarbonylpyrrol-1-yl)benzoate

HRID 399815Notes

Reaction equation

HRID 399815 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[N:6]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:7]=[CH:8][CH:9]=1)=[O:4].[CH2:22]([OH:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:22]([O:29][C:3]([C:5]1[N:6]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:7]=[CH:8][CH:9]=1)=[O:4])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 18945198Methyl 3-(2-trichloroacetylpyrrol-1-yl)benzoate

Product 1

HCID 18945465Methyl 3-(2-benzyloxycarbonylpyrrol-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of methyl 3-(2-trichloroacetylpyrrol-1-yl)benzoate (10.0 g), benzyl alcohol (3.3 ml) and potassium carbonate (4.4 g) in N,N-dimethylformamide (30 ml) was stirred for 6 hours at ambient temperature. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated. The residue was purified by column chromatography on silica gel eluting with toluene. The eluted fractions containing the desired product were collected and evaporated in vacuo to give methyl 3-(2-benzyloxycarbonylpyrrol-1-yl)benzoate (8.35 g) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel eluting with toluene
  6. additionThe eluted fractions containing the desired product
  7. customwere collected
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-c4199416c7264e3995d7385e14df8966
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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