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

HRID 1591059

반응식

HRID 1591059 반응식
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]

참가 물질

6

반응물 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 3034285Azoxystrobin

생성물 1

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

시약·촉매·용매 2

HCID 110158481-Hexanaminium, N,N,N-trihexyl-, sulfate (1:1)촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-999057fcfd924320bdaa271e01b1ca85
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05206245

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