Water → HCID 12897054, compound

HRID 1980996Notes

Reaction equation

HRID 1980996 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]1.[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(Cl)Cl.O>CCOCC>[C:10]([C:5]1[NH:1][CH:2]=[C:3]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 12361759methyl 1H-pyrrole-3-carboxylate

Product 1

HCID 12897054HCID 12897054, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under nitrogen, methyl pyrrole-3-carboxylate (5 g., 40 mmoles) was combined with benzoyl chloride (4.8 ml., 40 mmoles) and stannic chloride (9.2 ml. 80 mmoles) in 75 ml. of methylene chloride and stirred for 3 hours at room temperature. Ice and water (50 ml.) was added slowly and stirring continued for an additional 15 minutes. Ether (150 ml.) was then added and, after equilibration, the phases separated. The upper, organic phase was washed sequentially with 50 ml. of water, 50 ml. of 1N sodium hydroxide and 50 ml. of water, and evaporated to dryness to yield crude product (6.4 g. of solid). Recrystallization from acetonehexane gave purified methyl 5-benzoylpyrrole-3-carboxylate (4.1 g., Rf 0.4 on silica gel thin layer chromatography eluted with ethyl acetate-1/hexane-5/5% acetic acid).

Workup

  1. customafter equilibration, the phases separated
  2. washThe upper, organic phase was washed sequentially with 50 ml
  3. customof water, and evaporated to dryness

Sources & evidence

ORD record
ord-a0c7a131bf3541b9965a17c5f01e8148
Source dataset
uspto-grants-1985_04
Patent number
US04511576

Reaction notes

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