Cesium carbonate → Methyl 4-(6-quinaldinyloxy)-3-methylsulfonyl-benzoate

HRID 1684560ノート

反応式

HRID 1684560 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.Cl[C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[S:24]([CH3:27])(=[O:26])=[O:25].C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+]>CN(C)C(=O)N(C)C>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([O:1][C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=3[S:24]([CH3:27])(=[O:25])=[O:26])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:12]

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 5943956-Hydroxy-2-methylquinolineHCID 10490815Methyl 4-chloro-3-(methylsulfonyl)benzoate

生成物 1

HCID 67715635Methyl 4-(6-quinaldinyloxy)-3-methylsulfonyl-benzoate収率 85.4%

試薬・触媒・溶媒 1

HCID 12437Tetramethylurea溶媒

実験手順

2 g of 6-hydroxyquinaldine, 3.12 g of methyl 4-chloro-3-methylsulfonyl-benzoate and 12.28 g of Cs2CO3 are stirred in 50 ml of anhydrous tetramethylurea at 110° C. for 1 h. The mixture is cooled, 250 ml of saturated aqueous NaHCO3 solution are added and extraction is carried out 3 times with 125 ml of EA. The extracts are dried over Na2SO4, the solvent is removed in vacuo and the residue is chromatographed with MTB. 3.98 g of a colorless foam are obtained. Rf (MTB)=0.31 MS (ES): 372 (M+H)+

後処理

  1. temperatureThe mixture is cooled
  2. extractionextraction
  3. dry with materialThe extracts are dried over Na2SO4
  4. customthe solvent is removed in vacuo
  5. customthe residue is chromatographed with MTB

出典と根拠

ORDレコード
ord-68c3d2c20f4043c88fa17be9786cd7ed
出典データセット
uspto-grants-1997_06
特許番号
US05641792

反応ノート

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