Реакция #4533

Уравнение реакции

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

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.ADDITIONThis was followed by dropwise addition of a solution of 1.73 ml
2. 2
   Фильтрацияthe reaction mixture was filtered
3. 3
   ДругоеThe filtrate was evaporated to dryness in vacuo
4. 4
   workup.DISSOLUTIONthe residue was dissolved in 200 ml
5. 5
   ПромывкаThe resulting solution was washed successively with dilute hydrochloric acid and water
6. 6
   Сушкаdried with anhydrous sodium sulfate
7. 7
   ДругоеEvaporation in vacuo

Методика

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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