反応 #166058

反応方程式

p-xylene

3,5-diacetoxybenzoyl chloride

4-acetoxystyrene

→

resveratrol triacetate

収率 70.1%

溶媒

EtOAc

反応条件

後処理

1. 1
   温度Then it was cooled to room temperature
2. 2
   ろ過filtered
3. 3
   洗浄The filtrate was washed with brine
4. 4
   乾燥dried over Na2SO4
5. 5
   ろ過Then it was filtered
6. 6
   その他purified via flash chromatography (15% EtOAc/hexane, 25% EtOAc/Hexene

実験手順

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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