Dimethyl Sulfate → 4-methoxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran

HRID 38302노트

반응식

HRID 38302 반응식
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=O)[C:3]=1[C:10](=[O:25])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[C:15]([Cl:24])[CH:14]=1.[H-].[Na+].S(OC)(O[CH3:32])(=O)=O>CN(C)P(N(C)C)(N(C)C)=O>[CH3:32][O:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][CH2:4][C:3]=1[C:10](=[O:25])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[C:15]([Cl:24])[CH:14]=1

참가 물질

5

반응물 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 1363673424-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one

생성물 1

HCID 695121974-methoxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran

시약·촉매·용매 1

HCID 12679Hexamethylphosphoramide용매

실험 절차

In 4 ml of hexamethylphosphoramide was dissolved 0.33 g of 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one, to this solution was added 50 mg of sodium hydride (60% oily), and the mixture was stirred at room temperature for 30 minutes. Then, 0.2 ml of dimethyl sulfate was added, and the mixture was stirred at 65° C. for 1 hour, and at room temperature overnight. 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 subjected to silica gel column chromatography to obtain 0.13 g of 4-methoxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran [Compound No. (2a-17)] as a pale yellow crystal.

후처리

  1. stirringthe mixture was stirred at 65° C. for 1 hour
  2. customat room temperature
  3. customovernight
  4. extractionthis was extracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-facb536762614b55a1db9b571caac018
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524729B2

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