Methanol → Methyl pyrrole-2-carboxylate

HRID 1952534Notes

Reaction equation

HRID 1952534 reaction equation
ClC(Cl)(Cl)C([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=O.[C:12]([O-:15])([O-])=[O:13].[K+].[K+].[CH3:18]O>>[NH:6]1[CH:7]=[CH:8][CH:9]=[C:5]1[C:12]([O:15][CH3:18])=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 3214872-(Trichloroacetyl)pyrrole

Product 1

HCID 136930Methyl pyrrole-2-carboxylateYield 93%

Procedure

To a stirred solution of 2-(trichloroacetyl)pyrrole (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 (CDCl3) δ 9.49 (bs, 1H), 6.92-6.96 (m, 2H), 6.26 (m, 1H), and 3.86 (s, 3H); 13C NMR (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-8de4700319ef40ecb236af902fdd1e7a
Source dataset
uspto-grants-2013_03
Patent number
US08404728B2

Reaction notes

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