Methyl Acrylate → 4,5-Dihydro-5-(methoxycarbonyl)-3-isoxazolepropanoic acid methyl ester

HRID 653398

Reaktionsgleichung

Reaktionsgleichung von HRID 653398
[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH2:5][CH2:6][N+:7]([O-:9])=O.[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=[CH2:13].C(N(CC)CC)C.C1(N=C=O)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:16][O:15][C:11](=[O:14])[CH2:12][CH2:13][C:6]1[CH2:5][CH:4]([C:3]([O:2][CH3:1])=[O:10])[O:9][N:7]=1

Komponenten

6

Edukt 4

HCID 7294Methyl AcrylateHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 25604Methyl 4-nitrobutyrate

Produkt 1

HCID 139115534,5-Dihydro-5-(methoxycarbonyl)-3-isoxazolepropanoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 23.8 g of 4-nitrobutyric acid methyl ester (made in accordance with Bruson, U.S. Pat. No. 2,342,119) 39.6 g of methyl acrylate, 0.2 g triethyl amine in 200 ml of toluene is stirred and treated dropwise with 23.8 g of phenyl isocyanate. The mixture is stirred for 72 hours at room temperature and heated at 90° C. for two hours. The mixture is cooled, filtered to remove the diphyl urea, and concentrated under reduced pressure. The resulting oil is chromatographed on SiO2 (elution with hexane:ethyl-acetate; 75:25) to yield 4,5-dihydro-5-(methoxycarbonyl)-3-isoxazolepropanoic acid methyl ester as a colorless oil. NMR (CDCl3) and 4.93 (t, J=9 Hz, 1H), 3.72 (s, 3H), 3.63 (s, 3H), 3.20 (d, J-9 Hz, 2H9, 2.61 (s, 4H). IR (KBr) 2956, 2851, 1739, 1632, 1439, 1367, 1340, 1215. IR (cm-1).

Aufarbeitung

  1. temperatureheated at 90° C. for two hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customto remove the diphyl urea
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oil is chromatographed on SiO2 (elution with hexane:ethyl-acetate; 75:25)

Quellen und Nachweise

ORD-Eintrag
ord-39b3ead62885473aac7b69884bfc2550
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04677098

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