Ethanol → Ethyl 1H-pyrrole-3-carboxylate

HRID 456630Notes

Reaction equation

HRID 456630 reaction equation
[CH2:1]([OH:3])[CH3:2].[NH:4]1[CH:8]=[CH:7][C:6]([C:9](O)=[O:10])=[CH:5]1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:1]([O:3][C:9]([C:6]1[CH:7]=[CH:8][NH:4][CH:5]=1)=[O:10])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 101030Pyrrole-3-carboxylic acid

Product 1

HCID 13070719Ethyl 1H-pyrrole-3-carboxylateYield 81%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Ethanol (3.2 mL, 54 mmol) and 4-dimethylamino pyridine (DMAP) (54 mg, 0.45 mmol) were added to a mixture of pyrrole-3-carboxylic acid (500 mg, 4.5 mmol) and dicyclohexylcarbodiimide (1.11 g, 5.4 mmol) (Aldrich, Milwaukee, Wis.) in tetrahydrofuran (THF) (15 mL). After heating at 60° C. for 10 hours, the reaction was cooled. The precipitate was filtered off, washed with ethyl acetate, the combined filtrate was concentrated and purified on a silica gel column to give 500 mg (81%) of 1H-pyrrole-3-carboxylic acid ethyl ester as a colorless oil.

Workup

  1. temperaturethe reaction was cooled
  2. filtrationThe precipitate was filtered off
  3. washwashed with ethyl acetate
  4. concentrationthe combined filtrate was concentrated
  5. custompurified on a silica gel column

Sources & evidence

ORD record
ord-22c5c568d8d048c497a039d97808ee97
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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