Water → Methyl 2-(2-((6-(2-cyanophenoxy)pyrimidin-4-yl)oxy)phenyl)-2-oxoacetate

HRID 1591059

Reaktionsgleichung

Reaktionsgleichung von HRID 1591059
O.[C:2]([C:4]1[CH:31]=[CH:30][CH:29]=[CH:28][C:5]=1[O:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2/[C:20](=C\OC)/[C:21]([O:23][CH3:24])=[O:22])[CH:8]=1)#[N:3].[Mn]([O-])(=O)(=O)=[O:33].[K+]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCCCC)(CCCCCC)CCCCCC)CCCCC>[C:2]([C:4]1[CH:31]=[CH:30][CH:29]=[CH:28][C:5]=1[O:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20](=[O:33])[C:21]([O:23][CH3:24])=[O:22])[CH:8]=1)#[N:3]

Komponenten

6

Edukt 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 3034285Azoxystrobin

Produkt 1

HCID 15044819Methyl 2-(2-((6-(2-cyanophenoxy)pyrimidin-4-yl)oxy)phenyl)-2-oxoacetateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 110158481-Hexanaminium, N,N,N-trihexyl-, sulfate (1:1)KatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a vigorously stirred mixture of water (20 ml) and a solution of (E)-methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (3.2 g, 7.94 mmol) in dichloromethane (20 ml) was added potassium permanganate (2.5 g, 15.9 mmol) in one portion and tetra-n-hexylammonium hydrogen sulphate (200 mg). The reaction mixture was stirred overnight (16 hours) and then filtered. The filter was washed through with ether and water and then the combined filtrates were extracted with ether (×3). The ether extracts were washed with water (×3) and brine (×1), dried, filtered and evaporated. The residue was chromatographed (eluent dichloromethaneacetone, 98:2). Recrystallisation (ether-pentane) of the major component afforded methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-ketoacetate (2.105 g, 71%) as a white crystalline solid; mp 96°-97° C.; 1H NMR (CDCl3) δ 3.83(3H,s), 6.61(1H,s), 7.27-7.47(4H,m), 7.67-7.76(3H,m), 8.02(1H,dd), 8.39(1H,s) ppm; IR maxima 2234(CN), 1743(CO, ester); 1688(CO, ketone)cm-1.

Aufarbeitung

  1. filtrationfiltered
  2. washThe filter was washed through with ether and water
  3. extractionthe combined filtrates were extracted with ether (×3)
  4. washThe ether extracts were washed with water (×3) and brine (×1)
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed (eluent dichloromethaneacetone, 98:2)
  9. customRecrystallisation (ether-pentane) of the major component

Quellen und Nachweise

ORD-Eintrag
ord-999057fcfd924320bdaa271e01b1ca85
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05206245

Verknüpfte Notizen

Wird geladen…