Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-(5,6-dichloro-1H-indol-2-yl)-2-propenoate

HRID 1602999Notes

Reaction equation

HRID 1602999 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([CH:12]=O)=[CH:5]2.[CH2:14]([O:16][C:17]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:18])[CH3:15]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([CH:12]=[CH:19][C:17]([O:16][CH2:14][CH3:15])=[O:18])=[CH:5]2

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 108462775,6-dichloro-1H-indole-2-carbaldehyde

Product 1

HCID 53672814Ethyl 3-(5,6-dichloro-1H-indol-2-yl)-2-propenoateYield 60.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5,6-Dichloro-1H-indole-2-carboxaldehyde (35 g, 164 mmol) and (ethoxycarbonylmethylene)triphenylphosphorane (60 g, 176 mmol) were dissolved in toluene and refluxed for three hours. The solvent was evaporated under reduced pressure and the reaction mixture was purified by chromatography on silicagel (n-hexane/AcOEt, 8/2) obtaining pure title compound (28 g, 98.5 mmol, yield 60.1%).

Workup

  1. temperaturerefluxed for three hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe reaction mixture was purified by chromatography on silicagel (n-hexane/AcOEt, 8/2)

Sources & evidence

ORD record
ord-f4f86bb8b92b4077910e52361118af6a
Source dataset
uspto-grants-1999_11
Patent number
US05985905

Reaction notes

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