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HRID722864

反应详情

EQUATION

反应方程式

HRID 722864 的结构方程式

REACTANTS

反应物

4
结构：Cl
HCID313

Hydrochloric Acid

ClH

结构：Cc1ccc(S(=O)(=O)Cl)cc1
HCID7397

p-Toluenesulfonyl chloride

C7H7ClO2S

结构：CCN(CC)CC
HCID8471

Triethylamine

C6H15N

结构：CCC[C@@H](C)C[C@H](CO)CC(=O)OC(C)(C)C
HCID57070108

未命名化合物

PRODUCTS

生成物

1
结构：CCC[C@@H](C)C[C@H](COS(=O)(=O)c1ccc(C)cc1)CC(=O)OC(C)(C)C
HCID57178500

未命名化合物

收率 91.1%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CN(C)c1ccncc1
催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To alcohol 103 (1.98 g, 8.1 mmol) in CH2Cl2 (40 mL) at room temperature was added triethylamine (2.4 g, 0.024 mol), DMAP (20 mg) and tosyl chloride (2.3 g, 0.012 mol). After 14 hours 1N HCl was added and the two layers separated. The aqueous phase was extracted with ether and the combined organic phases dried (MgSO4) and concentrated. Flash chromatography (95% hexane/EtOAc) gave tosylate 104 as an oil (2.94 g, 91%). 13C NMR (100 MHz; CDCl3) 171.60, 144.92, 133.07, 130.02, 128.12, 80.80, 72.15, 39.73, 38.09, 37.89, 32.67, 29.71, 28.22, 21.83, 20.10, 19.54, 14.49.

WORKUP

后处理

  1. customthe two layers separated
  2. extractionThe aqueous phase was extracted with ether
  3. dry with materialthe combined organic phases dried (MgSO4)
  4. concentrationconcentrated