Pyridine → Trifluoromethanesulfonic acid 3-(4-chlorophenyl)-2-isopropyl-8-methoxy-4-oxo-4H-chromen-7-yl ester

HRID 14467

反応式

HRID 14467 の反応式
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:32](=[O:33])[C:31]3[C:26](=[C:27]([O:35][CH3:36])[C:28]([O-])=[CH:29][CH:30]=3)[O:25][C:24]=2[CH:37]([CH3:39])[CH3:38])=[CH:19][CH:18]=1.[Na+].ClC1C=CC(C2C(=O)C3C(=C(OC)C(O)=CC=3)OC=2C(C)C)=CC=1.[H-].[Na+].N1C=CC=CC=1>C(Cl)Cl.O1CCCC1.CN(C)C1C=CN=CC=1>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:32](=[O:33])[C:31]3[C:26](=[C:27]([O:35][CH3:36])[C:28]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:29][CH:30]=3)[O:25][C:24]=2[CH:37]([CH3:39])[CH3:38])=[CH:21][CH:22]=1

参加物

9

反応物 5

HCID 1049PyridineHCID 24758Sodium hydrideHCID 67749Trifluoromethanesulfonic anhydrideHCID 116026403-(4-Chlorophenyl)-7-hydroxy-2-isopropyl-8-methoxy-chromen-4-oneHCID 68702553sodium 3-(4-chlorophenyl)-2-isopropyl-8-methoxy-4-oxo-4H-chromen-7-olate

生成物 1

HCID 86625609Trifluoromethanesulfonic acid 3-(4-chlorophenyl)-2-isopropyl-8-methoxy-4-oxo-4H-chromen-7-yl ester

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of trifluoromethanesulfonic acid anhydride (3.5 g, 2.1 ml, 12.4 mmol, 2 eq.) in anhydrous methylene chloride (10 ml) is added dropwise to a stirred solution of sodium 3-(4-chlorophenyl)-2-isopropyl-8-methoxy-4-oxo-4H-chromen-7-olate (2.28 g, 6.22 mmol; prepared by treating 3-(4-chlorophenyl)-7-hydroxy-2-isopropyl-8-methoxy-chromen-4-one with a molar equivalent of sodium hydride in dry tetrahydrofuran), pyridine (2 g, 2.1 ml, 25.5 mmol, 4.1 eq.) and 4-dimethylaminopyridine (0.076 g, 0.62 mmol, 0.1 eq.) in anhydrous methylene chloride (60 ml) at 0° C. After stirring overnight, the solution is washed with 1M HCl solution. The organic phase is dried over anhydrous magnesium sulfate and filtered, and the solvent is removed by evaporation in vacuo to afford the title compound as a brown foam. The product is used in the next step without further purification.

後処理

  1. customprepared
  2. washthe solution is washed with 1M HCl solution
  3. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent is removed by evaporation in vacuo

出典と根拠

ORDレコード
ord-05226ec6f4434c27aabeb6b088529016
出典データセット
uspto-grants-2010_06
特許番号
US07732435B2

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