Реакция #55929

Уравнение реакции

sodium bicarbonate

8-acetoxy-2,6-dimethyl-5-hydroxy-2-octene

ethyl vinylether

p-toluenesulfonic acid monohydrate

→

8-acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene

Растворители

ether

ether

Условия реакции

Обработка

1. 1
   СушкаThe organic phase is dried (Na2SO4)
2. 2
   Другоеevaporated in vacuo
3. 3
   Другоеto give the crude product
4. 4
   ДругоеThe crude material is further purified by column chromatography on silica gel (25 g, 5% ethyl acetate in hexane)

Методика

A mixture of 8-acetoxy-2,6-dimethyl-5-hydroxy-2-octene (2.27 g, 10.6 mmole), ethyl vinylether (0.82 g. 11.4 mmole), p-toluenesulfonic acid monohydrate (catalytic amount) and ether (50 ml) is stirred at room temperature for 16 hours. The resulting mixture is treated with ether (150 ml) and washes with 5% sodium bicarbonate solution (2×100 ml). The organic phase is dried (Na2SO4), and evaporated in vacuo to give the crude product. The crude material is further purified by column chromatography on silica gel (25 g, 5% ethyl acetate in hexane) to give 8-acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene as a colorless oil.

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