Water → Methyl 1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylate

HRID 83592

Reaction equation

HRID 83592 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].C([O-])([O-])=O.[K+].[K+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Cl)=[CH:19][CH:18]=1.O>CN(C=O)C>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][N:1]2[CH:5]=[CH:4][CH:3]=[C:2]2[C:6]([O:8][CH3:9])=[O:7])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 136930Methyl pyrrole-2-carboxylate

Product 1

HCID 50900833Methyl 1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylateYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 1H-pyrrole-2-carboxylate (330 mg, 2.64 mmol) was dissolved in anhydrous DMF (8 mL). Solid K2CO3 (547 mg, 3.96 mmol) was added, followed by the addition of 1-chloro-4-(chloromethyl)benzene (638 mg, 3.96 mmol). The reaction was permitted to stir at 60° C. for 36 h, at which time the reaction was allowed to cool to rt. Water was added and the resulting precipitate was isolated over a filter, and dried under high vacuum overnight to give 570 mg of the title compound.

Workup

  1. temperatureto cool to rt
  2. customthe resulting precipitate was isolated over a filter
  3. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-d73f26653a394f2297a022d50ebf2dea
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Linked notes

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