反应 #82415

反应方程式

water

cyclohexane carboxaldehyde

Sodium hydride

trimethylsulfoxonium iodide

→

1-cyclohexyl ethylene oxide

收率 62.0%

溶剂

DMSO

Dimethyl sulfoxide

反应条件

后处理

1. 1
   其他equipped with a mechanical stirrer and an addition funnel
2. 2
   workup.ADDITIONhad been added
3. 3
   workup.ADDITIONGas was evolved throughout the addition
4. 4
   温度The reaction mixture was cooled to ambient temperature
5. 5
   萃取The aqueous solution was extracted with 3×100 mL of diethyl ether
6. 6
   洗涤The combined ether extracts were washed with water and brine
7. 7
   干燥dried over anhydrous magnesium sulfate
8. 8
   浓缩concentrated in vacuo
9. 9
   workup.DISTILLATIONThe crude product was distilled (44° C., 0.1 mm)

实验过程

Sodium hydride (4.5 g, 187.5 mmol) and trimethylsulfoxonium iodide (41.25 g, 187.5 mmol) were combined in a 3-neck flask equipped with a mechanical stirrer and an addition funnel. Dimethyl sulfoxide (DMSO) was added slowly, over a 30 min period, until 200 mL had been added. Gas was evolved throughout the addition. A solution of cyclohexane carboxaldehyde (21.8 mL, 180 mmol) in 50 mL of DMSO was added dropwise to the reaction mixture over a 15 min period. The reaction mixture was heated to 55° C. and stirred at 55° C. for 30 min. The reaction mixture was cooled to ambient temperature and poured into 500 mL of water. The aqueous solution was extracted with 3×100 mL of diethyl ether. The combined ether extracts were washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product was distilled (44° C., 0.1 mm) to give 14 g (62% yield) of 1-cyclohexyl ethylene oxide as a clear colorless liquid.

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