Реакция #166055

Уравнение реакции

p-xylene

3,5-diacetoxybenzoyl chloride

4-chloroacetoxystyrene

N-methyl morpholine

→

product

Выход 69.4%

3,5-diacetoxy-4′-chloroacetoxy stilbene

Выход 69.4%

Растворители

EtOAc

Условия реакции

Обработка

1. 1
   ТемператураThen it was cooled to room temperature
2. 2
   Фильтрацияfiltered
3. 3
   ПромывкаThe filtrate was washed with brine
4. 4
   Сушкаdried over Na2SO4
5. 5
   ФильтрацияThen it was filtered
6. 6
   Другоеpurified via flash chromatography

Методика

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.

Источник