反应 #949

ord-85a305aeebfc4263a0d5dfa4da2ff2f2

反应方程式

Cl
HCl
c1ccncc1
pyridine
Cc1ccc(S(=O)(=O)Cl)cc1
Tosyl chloride
CCN1C(=O)OCC1CO
product
CCN1C(=O)OCC1CO
(+-)-Ethyl-4-(hydroxymethyl)-2-oxazolidinone
CCC1(COS(=O)(=O)c2ccc(C)cc2)COC(=O)N1
beige solid
CCC1(COS(=O)(=O)c2ccc(C)cc2)COC(=O)N1
(+-)-4-Ethyl-4-[(tosyloxy)methyl]-2-oxazolidinone

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他to come to room temperature
  2. 2
    workup.STIRRINGstirred until solids
  3. 3
    过滤filtered
  4. 4
    洗涤washed with diethyl ether

实验过程

Tosyl chloride (142.2 g, Aldrich) was added to an ice-chilled solution of the product from step (a) (102.7 g) dissolved in pyridine (175 ml. Aldrich). The reaction mixture was stirred at ice bath temperature for six hours, then allowed to come to room temperature. The heterogeneous mixture was added to 1500 ml of a solution of brine and 1N HCl, stirred until solids appeared, filtered and washed with diethyl ether to give 194.6 g of a beige solid as the title product. 1H NMR consistent with the proposed structure.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US05723458uspto-grants-1998_03