反応 #166055

反応方程式

p-xylene

3,5-diacetoxybenzoyl chloride

4-chloroacetoxystyrene

N-methyl morpholine

→

product

収率 69.4%

3,5-diacetoxy-4′-chloroacetoxy stilbene

収率 69.4%

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

実験手順

A 10 mL round bottom flask was charged with p-xylene (4 mL), Pd II catalyst (4.5 mg, 0.02 mmol), 1,3-bis-(2,6-diisopropylphenyl)imidazolinium chloride (8.6 mg, 0.02 mmol), 3,5-diacetoxybenzoyl chloride (0.7695 g, 3 mmol), 4-chloroacetoxystyrene (0.393 g, 2 mmol), and N-methyl morpholine (0.276 g, 2.4 mmol). The mixture was stirred at 120° C. for 3.5 h under 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 and gave the product (0.54 g, 69.4%) as white solid. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.47 (d, 2H, J=8.7 Hz), 7.14-7.10 (m, 4H), 6.99 (q, 2H, J=16.2 Hz), 6.83 (t, 1H, J=2.1 Hz), 4.29 (s, 2H), 2.29 (s, 6H); 13C NMR (CDCl3, 75 MHz) δ 169.1, 165.9, 151.4, 150.1, 139.5, 135.1, 129.5, 127.9, 127.7, 121.6, 117.1, 114.7, 41.0, 21.2; HRMS (EI+) found 388.0710 M+, calcd 388.0714 for C20H17ClO6.

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