Реакция #55573

Уравнение реакции

1-(3-ethylcyclobutyl)-trans-3-iodoprop-2-en-1-ol

ethylvinyl ether

→

title compound

Выход 69.0%

1-iodo-3-(1-ethoxyethoxy)-3-(3-ethylcyclobutyl)-1E-propene

Выход 69.0%

Растворители

sodium bicarbonate

Условия реакции

Обработка

1. 1
   Другоеwas prepared
2. 2
   Экстракцияthe products were extracted with 150 ml (3×50 ml) of ether
3. 3
   ЭкстракцияThe combined ether extract
4. 4
   Промывкаwas washed with 50 ml of saturated aqueous sodium chloride
5. 5
   Сушкаdried over anhydrous magnesium sulfate
6. 6
   Фильтрацияfiltered
7. 7
   Другоеthe solvent was removed in vacuo
8. 8
   ДругоеThe residue was chromatographed on silica gel 60 (0.063-0.2 mm, 70-230 mesh, ASTM)

Методика

A mixture containing 4.8 g (0.018 mole) of 1-(3-ethylcyclobutyl)-trans-3-iodoprop-2-en-1-ol (prepared in 1I) and 38.2 g (50 ml, 0.51 mole) of ethylvinyl ether (Aldrich Chemical Company; Beilstein 1:433) was prepared. One drop of phosphorus oxychloride was added thereto and the mixture was allowed to stir for about 15 hr at room temperature. The mixture was poured into 50 ml of saturated aqueous sodium bicarbonate and the products were extracted with 150 ml (3×50 ml) of ether. The combined ether extract was washed with 50 ml of saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed in vacuo. The residue was chromatographed on silica gel 60 (0.063-0.2 mm, 70-230 mesh, ASTM) using chloroform as the eluant to yield 4.2 g of the title compound having the following physical characteristics:

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