反应 #4533

反应方程式

thionyl chloride

p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate

2,6-dimethylpyridine

→

title compound

p-Nitrobenzyl 2-(4-Ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate

溶剂

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   workup.ADDITIONThis was followed by dropwise addition of a solution of 1.73 ml
2. 2
   过滤the reaction mixture was filtered
3. 3
   其他The filtrate was evaporated to dryness in vacuo
4. 4
   workup.DISSOLUTIONthe residue was dissolved in 200 ml
5. 5
   洗涤The resulting solution was washed successively with dilute hydrochloric acid and water
6. 6
   干燥dried with anhydrous sodium sulfate
7. 7
   其他Evaporation in vacuo

实验过程

To a stirred solution of 6.8 g. of p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate in 200 ml. of tetrahydrofuran at 0°-5° C. was added 2.98 ml. of 2,6-dimethylpyridine. This was followed by dropwise addition of a solution of 1.73 ml. of thionyl chloride in 20 ml. of tetrahydrofuran, over a 5-minute period. Stirring was continued at 0°-5° C. for 15 minutes, and then the reaction mixture was filtered. The filtrate was evaporated to dryness in vacuo, and the residue was dissolved in 200 ml. of dichloromethane. The resulting solution was washed successively with dilute hydrochloric acid and water, and dried with anhydrous sodium sulfate. Evaporation in vacuo gave the title compound as a yellow, viscous liquid (yield: 7.12 g). The IR spectrum (CHCl3) of the product showed an absorption at 5.63 microns. The NMR spectrum (CDCl3) of the product showed absorptions at 1.3 (t, 3H); 2.47-3.7 (m, 4 H); 4.9-5.3 (m, 1H); 5.4 (s, 4H); 6.06 and 6.18 (ss, 1H); 7.58 (d, 2H); and 8.22 (d, 2H) ppm.

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