Water → 2-[(4-Chlorophenoxy)-methyl]-2-(1-ethoxycarbonyl-cycloprop-1-yl)-oxirane

HRID 704521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 704521
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH2:9]([O:11][C:12]([C:14]1([C:17]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[O:18])[CH2:16][CH2:15]1)=[O:13])[CH3:10].O>CS(C)=O>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][CH2:19][C:17]2([C:14]3([C:12]([O:11][CH2:9][CH3:10])=[O:13])[CH2:15][CH2:16]3)[CH2:4][O:18]2)=[CH:26][CH:25]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 14700140HCID 14700140, Verbindung

Produkt 1

HCID 147001412-[(4-Chlorophenoxy)-methyl]-2-(1-ethoxycarbonyl-cycloprop-1-yl)-oxiraneAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

3.6 g (0.13 mol) of 80% strength sodium hydride are added under an argon atmosphere and with stirring at 10° to 20° C. to a suspension of 24 g (0.11 mol) of trimethylsulphoxonium iodide in 100 ml of dimethyl sulphoxide. After stirring for 30 minutes at 20° C., 17.1 g (0.061 mol) of 4-chlorophenoxymethyl 1-ethoxycarbonylcycloprop-1-yl ketone are added. The mixture is warmed to 60° C. for 1 hour. After this, the mixture is poured into 300 ml of water and extracted with methylene chloride. The combined organic extracts are washed with water, dried over magnesium sulphate and concentrated. 14 g (77.8% of theory) of 2-[(4-chlorophenoxy)-methyl]-2-(1-ethoxycarbonyl-cycloprop-1-yl)-oxirane are obtained as an oil which is further reacted without additional purification. ##STR18##

Aufarbeitung

  1. temperatureThe mixture is warmed to 60° C. for 1 hour
  2. extractionextracted with methylene chloride
  3. washThe combined organic extracts are washed with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8b37f31efbce4f0cbea5d6b55a27dc20
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04988383

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