Water → Methyl 5-(2-methylbenzoyl)pyrrole-3-carboxylate

HRID 1980916Notes

Reaction equation

HRID 1980916 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]1.C(Cl)Cl.[C:13]1([CH3:22])[C:14]([C:19](Cl)=[O:20])=[CH:15][CH:16]=[CH:17][CH:18]=1.O>CCOCC>[CH3:22][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([C:5]1[NH:1][CH:2]=[C:3]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=1)=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6344Dichloromethane2×HCID 702762-Methylbenzoyl chlorideHCID 12361759methyl 1H-pyrrole-3-carboxylate

Product 1

HCID 12897056Methyl 5-(2-methylbenzoyl)pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under nitrogen at room temperature, methyl pyrrole-3-carboxylate (2.5 g., 20 mmoles) was combined with 75 ml. of methylene chloride. o-Toluoyl chloride (3.09 g., 20 mmoles) in 25 ml. of methylene chloride was added, followed by stannic chloride (4.6 ml., 40 mmoles) added at a fast dropwise rate via a needle and syringe. Progress of the reaction was followed by thin layer chromatography (silica gel with ethyl acetate-1/hexane-5/5% acetic acid as eluant). After stirring at room temperature for 2.5 hours, the reaction was cooled with an ice-water bath while 75 ml. of water was added dropwise. After addition was complete, the mixture was stirred for 15 minutes at room temperature, approximately an equal volume of ether was added, the organic layer separated, washed in sequence with water, 1N sodium hydroxide, water and saturated brine, dried over anhydrous sodium sulfate, filtered and evaporated to yield methyl 5-(2-methylbenzoyl)pyrrole-3-carboxylate.

Workup

  1. customat room temperature
  2. additionadded at a fast dropwise rate via a needle and syringe
  3. temperaturethe reaction was cooled with an ice-water bath while 75 ml
  4. additionAfter addition
  5. stirringthe mixture was stirred for 15 minutes at room temperature
  6. customthe organic layer separated
  7. washwashed in sequence with water, 1N sodium hydroxide, water and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-8cda3cb91c144964beeccc6aed82b057
Source dataset
uspto-grants-1985_04
Patent number
US04511575

Reaction notes

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