Реакция #42789

Уравнение реакции

7-amino-3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-chromen-4-one

NaHCO3

bromoacetylbromide

K2CO3

→

title compound

7-(4-Chlorophenyl)-6-isopropyl-1H-4,5-dioxa-1-aza-phenanthrene-2,8-dione

Растворители

dimethylformamide

Условия реакции

Обработка

1. 1
   Другоеto separate the organic phase, which
2. 2
   Температураheated in a microwave at 90° C. for 15 min
3. 3
   ДругоеThe reaction mixture is partitioned between CH2Cl2 and water
4. 4
   ПромывкаThe organic phase is washed with water and brine
5. 5
   Сушкаdried (MgSO4)
6. 6
   Концентрированиеconcentrated in vacuo
7. 7
   Другоеfollowed by crystallisation from methanol
8. 8
   ДругоеThe product is partitioned between ethyl acetate and water
9. 9
   Другоеto remove traces of dimethylformamide
10. 10
    СушкаThe organic phase is dried (MgSO4)
11. 11
    Концентрированиеconcentrated in vacuo
12. 12
    Другоеcrystallised from methanol

Методика

A mixture of 7-amino-3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-chromen-4-one (250 mg, 0.75 mmol), CDCl3 (1 ml), saturated NaHCO3 solution (1.5 ml) and bromoacetylbromide (169 mg, 0.85 mmol) is stirred vigorously at room temperature for 5 min and then passed through an Isolute™ phase separator to separate the organic phase, which is then treated with dimethylformamide (1 ml) and K2CO3 (115 mg, 0.85 mmol) and heated in a microwave at 90° C. for 15 min. The reaction mixture is partitioned between CH2Cl2 and water. The organic phase is washed with water and brine, dried (MgSO4) and concentrated in vacuo, followed by crystallisation from methanol. The product is partitioned between ethyl acetate and water to remove traces of dimethylformamide. The organic phase is dried (MgSO4), concentrated in vacuo and crystallised from methanol to yield the title compound.

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