Water → 4-[1-(1-Imidazolyl)-butyl]-trans-cinnamic acid ethyl ester

HRID 727860Notes

Reaction equation

HRID 727860 reaction equation
[N:1]1([CH:6]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)[CH2:7][CH2:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[C:18]([CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:20][CH2:21][CH3:22])=[O:19].O>O1CCOCC1>[CH2:21]([O:20][C:18](=[O:19])/[CH:23]=[CH:14]/[C:13]1[CH:16]=[CH:17][C:10]([CH:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH2:7][CH2:8][CH3:9])=[CH:11][CH:12]=1)[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 145143774-[1-(1-Imidazolyl)butyl]-benzaldehyde

Product 1

HCID 145143904-[1-(1-Imidazolyl)-butyl]-trans-cinnamic acid ethyl esterYield 50.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.228 g of 4-[1-(1-imidazolyl)-butyl]-benzaldehyde (example 6) is dissolved in 5 ml of dioxane and mixed with 0.35 g of carbethoxymethylene triphenyl phosphorane and stirred for 48 hours at room temperature. The reaction mixture is poured into 100 ml of water and extracted with ethyl acetate. The organic phases are combined and evaporated to dryness, the residue is distilled on a bulb tube. 0.15 g of the title compound with a boiling point of 200°-220° C./0.03 mbar is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. customevaporated to dryness
  3. distillationthe residue is distilled on a bulb tube

Sources & evidence

ORD record
ord-b32cfe472e254ec48abb8abe7316adc5
Source dataset
uspto-grants-1991_09
Patent number
US05045558

Reaction notes

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