Ethylene Glycol → HCID 20400896, compound

HRID 894074Notes

Reaction equation

HRID 894074 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)C[OH:22]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[C:12]([C:13]([O:15][CH2:16][CH2:17][OH:22])=[O:14])[NH:11][CH:10]=2)=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 174Ethylene GlycolHCID 73680293HCID 73680293, compound

Product 1

HCID 20400896HCID 20400896, compound

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 are 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
  7. customscale gave an additional 400 mg

Sources & evidence

ORD record
ord-37e5699eac9641a28dc2e440de306f27
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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