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

HRID 1870574Notes

Reaction equation

HRID 1870574 reaction equation
[CH2:1]([O:3][C:4](C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5])[CH3:2].[CH2:26]([N:28]([CH2:39][CH3:40])[C:29]1[CH:34]=[CH:33][C:32]([C:35](=O)[CH3:36])=[C:31]([OH:38])[CH:30]=1)[CH3:27].[C:41]1(C)C=CC=CC=1>>[CH2:1]([O:3][C:4](=[O:5])[CH:36]=[C:35]([C:32]1[CH:33]=[CH:34][C:29]([N:28]([CH2:39][CH3:40])[CH2:26][CH3:27])=[CH:30][C:31]=1[OH:38])[CH3:41])[CH3:2]

Participants

4

Reactant 3

HCID 1140TolueneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 47370991-(4-Diethylamino-2-hydroxy-phenyl)-ethanone

Product 1

HCID 540390873-(4-Diethylamino-2-hydroxy-phenyl)-but-2-enoic acid ethyl ester

Procedure

To a suspension of 5.27 g ethoxycarbonylmethylene-triphenylphosphorane 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.

Workup

  1. temperatureThen the reaction mixture was heated to reflux
  2. temperatureAfter refluxing for 31 hours the mixture
  3. temperaturewas cooled down
  4. customevaporated to dryness
  5. customThe resulting dark oil was purified by chromatography
  6. customto yield a colourless oil

Sources & evidence

ORD record
ord-4fff18dd2028428396211660adcb0a4d
Source dataset
uspto-grants-2000_08
Patent number
US06096918

Reaction notes

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