HCID 73680293, compound → HCID 20401055, compound

HRID 1981029Notes

Reaction equation

HRID 1981029 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7](=[CH:10][NH:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:8]=O)=[CH:4][CH:3]=1>C(O)CO>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:8]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 73680293HCID 73680293, compound

Product 1

HCID 20401055HCID 20401055, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

2-(4-Chlorophenoxy)-3-carbethoxymethylaminoacrylaldehyde (2 g.) was boiled in 5 ml. of ethylene glycol for 15 minutes. The reaction was cooled to room temperature, diluted with 10 ml. of water and product extracted into 10 ml. of ethyl acetate. The ethyl acetate was back-washed with water and concentrated to an oil (1.5 g.). The oil chromatographed on approximately 100 ml. of silica gel with ethyl acetate-1/hexane-1 as eluant, monitored by thin layer chromatography. Evaporation of middle fractions gave ethyl 4-(4-chlorophenoxy)pyrrole-2-carboxylate (100 mg., oil, m/e 281, Rf 0.65 on silica gel thin layer chromatography with ethyl acetate-1/hexane-1/5% acetic acid as eluant; Rf 0.3 with ethyl acetate-1/hexane-1 as eluant). Repeat on a 5.5 g. scale gave an additional 400 mg. of product.

Workup

  1. additiondiluted with 10 ml
  2. extractionof water and product extracted into 10 ml
  3. washThe ethyl acetate was back-washed with water
  4. concentrationconcentrated to an oil (1.5 g.)
  5. customThe oil chromatographed on approximately 100 ml
  6. customEvaporation of middle fractions

Sources & evidence

ORD record
ord-d8210cc7ab9c430c96bbc744314aa588
Source dataset
uspto-grants-1985_04
Patent number
US04511576

Reaction notes

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