Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 4-[2-[2-[(2-chloro)-ethoxy]-phenyl]-ethenyl]-1H-indole

HRID 1906192Notes

Reaction equation

HRID 1906192 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([CH:10]=[CH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.S(O[CH2:30][CH2:31][Cl:32])(C1C=CC(C)=CC=1)(=O)=O>[OH-].[Na+].O>[Cl:32][CH2:31][CH2:30][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:11]=[CH:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2

Participants

5

Reactant 2

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 541413862-[(1H-indol-4-yl)-ethenyl]-phenol

Product 1

HCID 542356984-[2-[2-[(2-chloro)-ethoxy]-phenyl]-ethenyl]-1H-indoleYield 39.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

4 g of 2-[(1H-indol-4-yl)-ethenyl]-phenol obtained in Step A of Example 1 in 100 ml of 2N sodium hydroxide after having added 6 g of 2-chloroethanol tosylate were heated for 6 hours at reflux and the mixture was left for 16 hours at ambient temperature, then diluted with water and extracted with ethyl acetate. After eliminating the solvent under reduced pressure and chromatography on silica (eluent: benzene), 2 g of 4-[2-[2-[(2-chloro)-ethoxy]-phenyl]-ethenyl]-1H-indole (trans E) were obtained.

Workup

  1. temperaturewere heated for 6 hours
  2. temperatureat reflux
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-f69f9a797ebb4410b183cea7efe2b7f4
Source dataset
uspto-grants-1987_03
Patent number
US04650811

Reaction notes

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