Water → HCID 12897075, compound

HRID 1981014Notes

Reaction equation

HRID 1981014 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.[CH:13]1([C:19](Cl)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O>CCOCC>[CH:13]1([C:19]([C:5]2[NH:1][CH:2]=[C:3]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=2)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 75938Cyclohexanecarbonyl chlorideHCID 12361759methyl 1H-pyrrole-3-carboxylate

Product 1

HCID 12897075HCID 12897075, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl pyrrole-3-carboxylate (1.25 g., 10 mmoles) in 25 ml. of methylene chloride under nitrogen, was added cyclohexanecarbonyl chloride (1.46 g., 1.33 ml., 10 mmoles) and then stannic chloride (3.13 g., 1.4 ml., 14 mmoles). The resulting solution was stirred 3 hours at room temperature, then 15 ml. of water added slowly and finally 50 ml. of ether. The organic phase was separated, washed with 20 ml. of water, filtered and evaporated to yield methyl 5-cyclohexylcarbonylpyrrole-3-carboxylate (Rf 0.25 on silica gel thin layer chromatography with ethyl acetate-1/hexane-5/5% acetic acid as eluant). The entire batch was used, without weight determination, in the next step.

Workup

  1. customThe organic phase was separated
  2. washwashed with 20 ml
  3. filtrationof water, filtered
  4. customevaporated

Sources & evidence

ORD record
ord-07057479c020488fa93b19d3c1d54862
Source dataset
uspto-grants-1985_04
Patent number
US04511576

Reaction notes

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