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

HRID 1591059

反応式

HRID 1591059 の反応式
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]

参加物

6

反応物 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 3034285Azoxystrobin

生成物 1

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

試薬・触媒・溶媒 2

HCID 110158481-Hexanaminium, N,N,N-trihexyl-, sulfate (1:1)触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-999057fcfd924320bdaa271e01b1ca85
出典データセット
uspto-grants-1993_04
特許番号
US05206245

関連ノート

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