반응 #166058

반응 방정식

p-xylene

3,5-diacetoxybenzoyl chloride

4-acetoxystyrene

→

resveratrol triacetate

수율 70.1%

용매

EtOAc

반응 조건

후처리

1. 1
   온도Then it was cooled to room temperature
2. 2
   여과filtered
3. 3
   세척The filtrate was washed with brine
4. 4
   건조dried over Na2SO4
5. 5
   여과Then it was filtered
6. 6
   기타purified via flash chromatography (15% EtOAc/hexane, 25% EtOAc/Hexene

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) δ 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.

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