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HRID558021

反应详情

EQUATION

反应方程式

HRID 558021 的结构方程式

REACTANTS

反应物

2
结构：ClCCl
HCID6344

Dichloromethane

CH2Cl2

结构：CCOP(=O)(C[C@H]1O[C@H](COCc2ccccc2)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@@H]1N=[N+]=[N-])OCC
HCID15946645

未命名化合物

PRODUCTS

生成物

1
结构：CCOP(=O)(C[C@H]1O[C@H](COC(C)=O)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@@H]1N=[N+]=[N-])OCC
HCID15946646

未命名化合物

收率 169.2%

AUXILIARIES

试剂、催化剂与溶剂

3
结构：O=S(=O)(O)O
催化剂HCID1118

Sulfuric acid

H2O4S

结构：CC(=O)OC(C)=O
溶剂HCID7918

Acetic anhydride

C4H6O3

结构：CC(=O)O.CC(=O)OC(C)=O
溶剂HCID21895370

未命名化合物

PROCEDURE

实验过程

Compound 3 (3.2 g, 5.2 mmol) was dissolved in HOAc/Ac2O (1:1, 32 mL). Ten drops of 1% H2SO4 in Ac2O was added. After stirring overnight the mixture was poured into a separation funnel containing ice and CH2Cl2. The organic phase was separated, filtered through a plug of silica and concentrated. The residue was purified by column chromatography to give 4 (2.48 g, 4.4 mmol, 84%). 13C-NMR (CDCl3) 170.41, 137.41, 136.95, 128.34-127.75, 77.77, 77.60, 74.01, 73.39, 72.17, 71.89, 69.26, 62.47, 61.82, 61.73, 60.50, 60.37, 27.57 (d, J=141 Hz), 20.59, 16.27, 16.19; 31P-NMR (CDCl3) 27.50; [α]D+37 (c 1.0, CHCl3).

WORKUP

后处理

  1. additionwas poured into a separation funnel
  2. customThe organic phase was separated
  3. filtrationfiltered through a plug of silica
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography