Potassium Carbonate → 2-(2,4-Dichlorophenyl)-5-(oxiran-2-ylmethoxy)benzoxazole

HRID 22726

Reaktionsgleichung

Reaktionsgleichung von HRID 22726
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:12]=2[N:13]=1.[CH2:19]([C@H:21]1[O:23][CH2:22]1)Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH:21]3[CH2:22][O:23]3)=[CH:14][C:12]=2[N:13]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 149428(+)-EpichlorohydrinHCID 219117282-(2,4-Dichlorophenyl)benzoxazol-5-ol2×

Produkt 1

HCID 219116592-(2,4-Dichlorophenyl)-5-(oxiran-2-ylmethoxy)benzoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 2-(2,4-dichlorophenyl)benzoxazol-5-ol, a compound of formula (g) (6.0 g, 36 mmol), (S)-(+)-epichlorohydrin (3.3 g, 315 mmol), a compound of formula (b) (20 ml, 182 mmol), and potassium carbonate (20 g, 144 mmol) in acetone (100 ml) was heated to reflux and stirred overnight. The solution was allowed to cool and filtered through Celite 512. The filtrate was evaporated under reduced pressure, to yield an oil. The oil was chromatographed on silica gel, eluting with 20% ethyl acetate/hexanes, to provide 2-(2,4-dichlorophenyl)-5-(oxiran-2-ylmethoxy)benzoxazole as a white solid (6.2 g, 28 mmol).

Aufarbeitung

  1. temperatureto reflux
  2. temperatureto cool
  3. filtrationfiltered through Celite 512
  4. customThe filtrate was evaporated under reduced pressure
  5. customto yield an oil
  6. customThe oil was chromatographed on silica gel
  7. washeluting with 20% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d72bb1d66a474182a6dd290f9bff2a63
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849632B2

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