Dimethylformamide → Methyl 1-(3,5-dibenzyloxybenzyl)-4-phenyl-3-pyrrolecarboxylate

HRID 350089Notes

Reaction equation

HRID 350089 reaction equation
[H-].[Na+].[C:3]1([C:9]2[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][NH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CS(O[CH2:23][C:24]1[CH:29]=[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]=[C:26]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:25]=1)(=O)=O.CN(C)C=O>O>[CH2:39]([O:38][C:26]1[CH:25]=[C:24]([CH:29]=[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]=1)[CH2:23][N:12]1[CH:13]=[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11]1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 5142464Methyl 4-phenyl-1H-pyrrole-3-carboxylateHCID 230248183,5-Dibenzyloxybenzyl methanesulfonate

Product 1

HCID 23025021Methyl 1-(3,5-dibenzyloxybenzyl)-4-phenyl-3-pyrrolecarboxylateYield 95.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60%, oily, 2.20 g) was added to a mixture of methyl 4-phenylpyrrole-3-carboxylate (11.10 g), 3,5-dibenzyloxybenzyl methanesulfonate (21.9 g) and N,N-dimethylformamide (200 ml) at 0° C., and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water, then with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography, and methyl 1-(3,5-dibenzyloxybenzyl)-4-phenylpyrrole-3-carboxylate (26.4 g, yield: 95%) was obtained as an oily substance from the fraction eluted with tetrahydrofuran-hexane (1:2, volume ratio).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c4fa5804464e4c3b915b496fb2c2b580
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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