Dimethyl Sulfate → (1E,6E)-1-(3,4-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

HRID 520788노트

반응식

HRID 520788 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10](=[O:25])[CH2:11][C:12](=[O:24])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:23])[CH:16]=2)=[CH:4][C:3]=1[O:26][CH3:27].[C:28]([O-])([O-])=O.[K+].[K+].COS(=O)(=O)OC>CC(C)=O.O>[CH3:27][O:26][C:3]1[CH:4]=[C:5](/[CH:8]=[CH:9]/[C:10](=[O:25])[CH2:11][C:12](=[O:24])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:23])[CH:16]=2)[CH:6]=[CH:7][C:2]=1[O:1][CH3:28]

참가 물질

6

반응물 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 969516Curcumin

생성물 1

HCID 10249311(1E,6E)-1-(3,4-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione수율 44.5%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

To the solution of (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (368 mg, 1.0 mmol, 1.0 eq.) in dry acetone (10 mL) were added anhydrous K2CO3 (138 mg, 1.0 mmol, 1.0 eq.) and sulfuric acid dimethyl ester (176 mg, 1.0 mmol, 1.0 eq.) at rt. The reaction mixture was heated under reflux overnight, cooled, diluted with water and extracted with CH2Cl2 (30 mL×3). The combined organic layers were washed with H2O, dried over anhydrous Na2SO4 and concentrated. The resulting residue was purified by silica column chromatography using CH2Cl2 as eluent to provide (1E,6E)-1-(3,4-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (170 mg, 44%).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. temperaturecooled
  4. extractionextracted with CH2Cl2 (30 mL×3)
  5. washThe combined organic layers were washed with H2O
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica column chromatography

출처 및 근거

ORD 기록
ord-3e7a97d868ea4569a5f92d9f76263601
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328081B2

반응 노트

불러오는 중…