Hydrochloric Acid → Methyl 1-(4-benzyloxybenzyl)-4-phenylpyrrole-3-carboxylate

HRID 350029

Reaction equation

HRID 350029 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.[CH2:18]([O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>CN(C)C=O>[CH2:18]([O:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:30][N:12]2[CH:13]=[C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11]2)=[CH:32][CH:33]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 700424-Benzyloxybenzyl chlorideHCID 5142464Methyl 4-phenyl-1H-pyrrole-3-carboxylate

Product 1

HCID 23024961Methyl 1-(4-benzyloxybenzyl)-4-phenylpyrrole-3-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, oily, 2.55 g) was added to a mixture of methyl 4-phenylpyrrole-3-carboxylate (11.61 g), 4-benzyloxybenzyl chloride (15.23 g) and N,N-dimethylformamide (100 ml) at 0° C., and the mixture was stirred for one hour. The reaction mixture was poured into dilute hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and methyl 1-(4-benzyloxybenzyl)-4-phenylpyrrole-3-carboxylate (22.16 g, yield: 97%) was obtained from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 97–98° C.

Workup

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

Sources & evidence

ORD record
ord-160fdf1a69ab41f684c6ecb2ba79a8f1
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Linked notes

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