Dimethyl Sulfate → 4-methoxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one

HRID 38304

반응식

HRID 38304 반응식
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4](=[O:12])[C:3]=1[C:13](=[O:28])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[C:18]([Cl:27])[CH:17]=1.[H-].[Na+].S(OC)(O[CH3:35])(=O)=O>CN(C)P(N(C)C)(N(C)C)=O>[CH3:35][O:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4](=[O:12])[C:3]=1[C:13](=[O:28])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[C:18]([Cl:27])[CH:17]=1

참가 물질

5

반응물 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 762111144-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]1-oxo-2-propenyl]-2H-1-benzopyran-2-one

생성물 1

HCID 740199914-methoxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one

시약·촉매·용매 1

HCID 12679Hexamethylphosphoramide용매

실험 절차

In 15 ml of hexamethylphosphoramide was dissolved 1.37 g of 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]1-oxo-2-propenyl]-2H-1-benzopyran-2-one, to this solution was added 0.17 g of sodium hydride (60% oily), and this was stirred at room temperature for 30 minutes. Then, 0.8 ml of dimethyl sulfate, and this was stirred at 65° C. for 2 hours. Thereafter, the reaction mixture was added to ice water, and this was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was washed with t-butyl methyl ether to obtain 0.38 g of 4-methoxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one [Compound No. (2c-17)] as a pale yellow crystal.

후처리

  1. extractionthis was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washThe residue was washed with t-butyl methyl ether

출처 및 근거

ORD 기록
ord-75dfcb2215cb4145b0e850ce7d13f174
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524729B2

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