Water → HCID 12897083, compound

HRID 1981019Notes

Reaction equation

HRID 1981019 reaction equation
[CH3:1][C:2]1[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][NH:5][CH:6]=1.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(Cl)Cl.O>CCOCC>[CH3:1][C:2]1[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][NH:5][C:6]=1[C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 235044Ethyl 4-methyl-1h-pyrrole-3-carboxylate

Product 1

HCID 12897083HCID 12897083, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl 4-methylpyrrole-3-carboxylate (920 mg., 6 mmoles) was combined with benzoyl chloride (0.7 ml., 6 mmoles), stannic chloride (1.2 ml., 12 mmoles) in 25 ml. of methylene chloride and stirred under nitrogen for 2 hours at room temperature. Water (15 ml.) was added slowly, dissolving the precipitate which had formed. Ether (50 ml.) was then added, and the organic phase separated, back-washed with 20 ml. of water, and evaporated to an oil. The oil was triturated with hexane to yield crystalline product (1.12 g.). Recrystallization from acetone/hexane afforded purified ethyl 4-methyl-5-benzoylpyrrole-3-carboxylate (900 mg., m.p. 127°-129° C.).

Workup

  1. dissolutiondissolving the precipitate which
  2. customhad formed
  3. customthe organic phase separated
  4. washback-washed with 20 ml
  5. customof water, and evaporated to an oil
  6. customThe oil was triturated with hexane
  7. customto yield crystalline product (1.12 g.)
  8. customRecrystallization from acetone/hexane
  9. customafforded
  10. custompurified ethyl 4-methyl-5-benzoylpyrrole-3-carboxylate (900 mg., m.p. 127°-129° C.)

Sources & evidence

ORD record
ord-757e63bc0fcd4ec29f5668590e6b97b4
Source dataset
uspto-grants-1985_04
Patent number
US04511576

Reaction notes

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