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

HRID 14467

반응식

HRID 14467 반응식
[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

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-05226ec6f4434c27aabeb6b088529016
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732435B2

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