Methanol → Methyl 5-(4-chlorophenyl)-1H-pyrrole-2-carboxylate

HRID 1975204Notes

Reaction equation

HRID 1975204 reaction equation
[CH3:1][O-:2].[Na+].ClC(C([C:10]1([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[N:14]=[CH:13][CH:12]=[CH:11]1)=O)(Cl)Cl.[CH3:22][OH:23]>O>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:10]2[NH:14][C:13]([C:1]([O:23][CH3:22])=[O:2])=[CH:12][CH:11]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 189303945-(p-Chlorophenyl)pyrrol-5-yl trichloromethyl ketone

Product 1

HCID 18930419Methyl 5-(4-chlorophenyl)-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium methoxide (12.73 mL of 4.38 M solution in methanol, 0.0556 mol) in methanol is cooled with an ice bath, treated with 5-(p-chlorophenyl)pyrrol-5-yl trichloromethyl ketone (6.0 g, 0.0186 mol), stirred for two hours, diluted with water and filtered to obtain a solid. The solid is washed with water and dried overnight in a vacuum dessicator to give the title product as a tan solid (4.23 g, mp 177°-179° C.) which is identified by 1HNMR spectral analysis.

Workup

  1. filtrationfiltered
  2. customto obtain a solid
  3. washThe solid is washed with water
  4. customdried overnight in a vacuum dessicator

Sources & evidence

ORD record
ord-92e78b1191e94054b8505db549ea86c4
Source dataset
uspto-grants-1994_02
Patent number
US05284863

Reaction notes

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