Potassium Carbonate → Methyl pyrrole-2-carboxylate

HRID 1952519Notes

Reaction equation

HRID 1952519 reaction equation
BrCC1C=C(C=CC=1)C[N:7]1[C:11](I)=[C:10](C=O)[CH:9]=[C:8]1[C:15]([O:17][CH3:18])=[O:16].C([O-])([O-])=O.[K+].[K+]>CO>[NH:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86664852HCID 86664852, compound

Product 1

HCID 136930Methyl pyrrole-2-carboxylateYield 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-(trichloroacetyl)pyrrole (1) (10.00 g, 47.1 mmol) in MeOH (20 mL) was added K2CO3 (8.44 g, 61.2 mmol). The resulting mixture was stirred under reflux for 3 hours, cooled to room temperature and filtered. The filtrate was concentrated in vacuo to give 2 as a dark brown solid (5.50 g, 93%). 1H NMR (400 MHz, CDCl3) δ 9.49 (brs, 1H), 6.92-6.96 (m, 2H), 6.26 (m, 1H), and 3.86 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 162.05, 123.33, 122.79, 115.56, 110.66, and 51.72.

Workup

  1. temperatureunder reflux for 3 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-928795c34fb6421ab72f5a86e60ff177
Source dataset
uspto-grants-2013_03
Patent number
US08404728B2

Reaction notes

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