Reaction #172475

Reaction equation

water

3-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]-5,5-dimethyl-2-cyclohexenone

sodium hydride

diethyl cyanomethylphosphonate

→

[3-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]-5,5-dimethyl-2-cyclohexenylidene]acetonitrile

Yield 82.0%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   Extractionextraction with ethyl acetate
2. 2
   WashThe extract was washed with a saturated saline solution
3. 3
   Dryingdried over anhydrous sodium sulfate
4. 4
   Concentrationconcentrated
5. 5
   OtherThe residue was purified by silica gel column chromatography
6. 6
   Otherto give 1.05 g of an orange oily matter (yield: 82.0%)

Procedure

To 0.23 g (9.6 mmol) of sodium hydride, 20 ml of tetrahydrofuran was added. To this mixture, 1.39 g (7.85 mmol) of diethyl cyanomethylphosphonate was added dropwise under ice cooling. To the mixture, 1.21 g (3.15 mmol) of 3-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]-5,5-dimethyl-2-cyclohexenone in tetrahydrofuran was added dropwise. After the reaction mixture was stirred at 50° C. overnight, water was added thereto and extraction with ethyl acetate was performed. The extract was washed with a saturated saline solution, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give 1.05 g of an orange oily matter (yield: 82.0%).

Source