Reaction #742249

Reaction equation

ethoxycarbonylmethylenetriphenylphosphorane

toluene

1-(4-diethylamino-2-hydroxy-phenyl)ethanone

→

3(4-Diethylamino-2-hydroxy-phenyl)-but-2-enoic acid ethyl ester

Conditions

Workup

1. 1
   TemperatureThen the reaction mixture was heated to reflux
2. 2
   TemperatureAfter refluxing for 31 hours the mixture
3. 3
   Temperaturewas cooled down
4. 4
   Otherevaporated to dryness
5. 5
   OtherThe resulting dark oil was purified by chromatography
6. 6
   Otherto yield a colourless oil

Procedure

To a suspension of 5.27 g ethoxycarbonylmethylenetriphenylphosphorane in 10 ml of toluene, a solution of 2.02 g 1-(4-diethylamino-2-hydroxy-phenyl)ethanone (DE 28 44 606) was dropped in at room temperature. Then the reaction mixture was heated to reflux. After refluxing for 31 hours the mixture was cooled down and evaporated to dryness. The resulting dark oil was purified by chromatography to yield a colourless oil.

Source