Phenol, 4-bromo-, 1-acetate → Triacetylresveratrol

HRID 1163270

반응식

HRID 1163270 반응식
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:13][C:14](=[O:16])[CH3:15])[CH:12]=1)[CH:8]=[CH2:9])(=[O:3])[CH3:2].[C:17]([O:20][C:21]1[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=1)(=[O:19])[CH3:18].C([O-])(O)=O.[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:4][C:5]1[CH:6]=[C:7](/[CH:8]=[CH:9]/[C:24]2[CH:25]=[CH:26][C:21]([O:20][C:17](=[O:19])[CH3:18])=[CH:22][CH:23]=2)[CH:10]=[C:11]([O:13][C:14](=[O:16])[CH3:15])[CH:12]=1)(=[O:3])[CH3:2]

참가 물질

7

반응물 3

HCID 74726Phenol, 4-bromo-, 1-acetateHCID 516892Sodium BicarbonateHCID 113105593,5-Diacetoxy Styrene

생성물 1

HCID 5962587Triacetylresveratrol

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매2회

반응 조건

온도
100 °C

실험 절차

A flask equipped with magnetic stirrer was charged with 50 mg (0.23 mmol, 1 eq) of 3,5-diacetoxystyrene, 49 mg (0.23 mmol) of 4-acetoxybromobenzene, 46 mg (0.27 mmol) of NaHCO3 and 78 mg (0.54 mmol, 2.4 eq) of tetrabutylammoniumchloride. The reactants were suspended in 2 ml DMF and the mixture was flushed with argon and then evacuated. The argon flushing and evacuation procedure was carried out three times. The reaction was started by adding 0.76 mg of palladium acetate in 50 μl of de-aerated DMF (3 μmol, 1.5 mol %), and stirred at 100° C. for three hours. Work-up of the reaction mixture following the procedure of Example 5 gave (E)-3,4′,5-triacetoxystilbene.

후처리

  1. customA flask equipped with magnetic stirrer
  2. customthe mixture was flushed with argon
  3. customevacuated

출처 및 근거

ORD 기록
ord-c1bbab8e0da74da3ae16839899640c2c
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820848B2

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