P-Xylene → Resveratrol triacetate

HRID 2236337

반응식

HRID 2236337 반응식
CC1C=CC(C)=CC=1.[C:9]([O:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([O:22][C:23](=[O:25])[CH3:24])[CH:21]=1)[C:16](Cl)=O)(=[O:11])[CH3:10].[C:26]([O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=C)=[CH:32][CH:31]=1)(=[O:28])[CH3:27]>CC([O-])=O.CC([O-])=O.[Pd+2].[Cl-].C(C1C=CC=C(C(C)C)C=1[NH+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C1)(C)C.CCOC(C)=O>[C:9]([O:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:34][C:33]2[CH:36]=[CH:37][C:30]([O:29][C:26](=[O:28])[CH3:27])=[CH:31][CH:32]=2)[CH:19]=[C:20]([O:22][C:23](=[O:25])[CH3:24])[CH:21]=1)(=[O:11])[CH3:10]

참가 물질

7

반응물 3

HCID 7809P-XyleneHCID 758214-Ethenylphenyl acetateHCID 11368883(3-Acetyloxy-5-carbonochloridoylphenyl) acetate

생성물 1

HCID 3935161Resveratrol triacetate수율 70.1%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 184547821,3-BIS(2,6-DIISOPROPYLPHENYL)imidazoLIDINIUM-CHLORIDE촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

A 100 mL round bottom flask was charged with p-xylene (56 mL), Pd(OAc)2 (62.86 mg, 0.28 mmol), 1,3-bis-(2,6-diisopropylphenyl) imidazolinium chloride (119.53 mg, 0.28 mmol), 3,5-diacetoxybenzoyl chloride (7.19 g, 28 mmol), 4-acetoxystyrene (5.35 mL, 33.6 mmol), and N-methyl morphorline (4.2 mL, 33.6 mmol). The mixture was stirred at 120° C. for 3.5 h at nitrogen atmosphere. Then it was cooled to room temperature and EtOAc was added and filtered. The filtrate was washed with brine and dried over Na2SO4. Then it was filtered and purified via flash chromatography (15% EtOAc/hexane, 25% EtOAc/Hexene, then 35% EtOAc/hexane) and gave resveratrol triacetate (6.95 g, 70.1%) as white solid. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.50 (d, 2H), 7.12-6.94 (m, 6H), 6.82 (t, 1H), 2.31 (s, 9H); 13C NMR (CDCl3, 75 MHz) 169.6, 169.2, 151.5, 150.6, 139.7, 134.7, 129.9, 127.9, 127.4, 122.1, 117.1, 114.6, 21.4; mp=116-118° C.; HRMS (EI+) found 354.1118 M+, calcd 354.1103 for C20H18O6; Anal. Calcd for C20H18O6: C, 67.79, H, 5.12. Found: C, 67.93, H, 5.26.

후처리

  1. temperatureThen it was cooled to room temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationThen it was filtered
  6. custompurified via flash chromatography (15% EtOAc/hexane, 25% EtOAc/Hexene

출처 및 근거

ORD 기록
ord-aa7333d3f8f449b99f93e3f5ae7e9a63
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07714161B2

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