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

HRID 520788ノート

反応式

HRID 520788 の反応式
[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]

参加物

6

反応物 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 969516Curcumin

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-3e7a97d868ea4569a5f92d9f76263601
出典データセット
uspto-grants-2016_05
特許番号
US09328081B2

反応ノート

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