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HRID1659856

反应详情

EQUATION

反应方程式

HRID 1659856 的结构方程式

REACTANTS

反应物

2
结构：CCOc1ccc2c(c1)C(C)=CC(C)(C)N2
HCID3293

Ethoxyquin

C14H19NO

结构：CC(=O)N[C@]1(O)C(Cl)O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
HCID54014248

未命名化合物

PRODUCTS

生成物

1
结构：CCOc1ccc2c(c1)C(C)=CC(C)(C)N2C1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1NC(C)=O
HCID54439761

未命名化合物

收率 63%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CC(C)=O
溶剂HCID180

Acetone

C3H6O

PROCEDURE

实验过程

2-Acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl chloride (18.3 g) and ethoxyquin (22.1 g) were vigorously stirred together at 80° for 3 hours. Acetone (50 ml) was added to the hot reaction mixture and stirring was continued for 0.5 hours. After cooling, the solid ethoxyquin-hydrochloride was filtered, washed with acetone and the combined filtrates were evaporated under reduced pressure. The crude product was purified by column chromatography on silica (ethylacetate-benzene 1:4). 16.5 g of 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosyl)-6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline were obtained. Analytical grade sample was obtained by recrystallisation from ether or isopropanol. m.p. 186°-187°.

WORKUP

后处理

  1. temperatureAfter cooling
  2. filtrationthe solid ethoxyquin-hydrochloride was filtered
  3. washwashed with acetone
  4. customthe combined filtrates were evaporated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica (ethylacetate-benzene 1:4)