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Water → 5-Oxo-2-phenoxythiocarbonyl-2,5-dihydro-isoxazole-4-carboxylic acid ethyl ester

HRID 2080116
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2080116
[CH2:1]([O:3][C:4]([C:6]1[C:10](=[O:11])[O:9][NH:8][CH:7]=1)=[O:5])[CH3:2].[CH:12]1[CH:17]=[CH:16][C:15]([O:18][C:19](Cl)=[S:20])=[CH:14][CH:13]=1.N1C=CC=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:10](=[O:11])[O:9][N:8]([C:19]([O:18][C:15]2[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=2)=[S:20])[CH:7]=1)=[O:5])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 70498Phenyl thioxochloroformateHCID 239539Ethyl 5-Hydroxy-4-isoxazolecarboxylate

Produkt 1

HCID 105656355-Oxo-2-phenoxythiocarbonyl-2,5-dihydro-isoxazole-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

5-Oxo-2,5-dihydro-isoxazole-4-carboxylic acid ethyl ester described in Preparation Example 112 (1.00 g, 5.17 mmol), phenyl chlorothionoformate (786 μl, 5.69 mmol) and pyridine (919 μl, 11.4 mmol) were dissolved at 0° C. in toluene (20 mL), and the solution was stirred at room temperature for 17 hours under nitrogen atmosphere. Water was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, and the organic layer was washed with brine. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), and the title compound (1.66 g, 5.66 mmol, quantitatively) was obtained as a pale yellow solid.

Aufarbeitung

  1. extractionwhich was then extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-08918559b62342e291cb36403491f6cf
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07932272B2

Notizen zur Reaktion

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