Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → HCID 18469778, compound

HRID 2228370Notes

Reaction equation

HRID 2228370 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2.[Cl:14][CH2:15][CH2:16]OS(C1C=CC(C)=CC=1)(=O)=O>O1CCCC1>[Cl:14][CH2:15][CH2:16][N:10]1[C:11]2[C:7](=[CH:6][C:5]([O:4][CH3:3])=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

5

Reactant 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 138725-MethoxyindoleHCID 24758Sodium hydride

Product 1

HCID 18469778HCID 18469778, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a flask of 500 ml capacity fitted with a stirrer and cooling tube, there were introduced 7.2 g (corresponding to 0.21 mol) of an oil dispersion of NaH, and 50 ml of tetrahydrofuran, and stirred on an ice-water bath. To this mixture there was added dropwise, a little at a time, a solution of 30.87 g (0.21 mol) of 5-methoxyindole dissolved in 100 ml of tetrahydrofuran. After completion of the dropwise addition, the ice-water bath was removed and the mixture was cooled for one hour at room temperature. Then, 49.29 g (0.21 mol) of 2-chloroethyl-p-toluene sulfonate were added, and reacted for 15 hours while stirring, heating under reflux. After completion of the reaction, the insoluble material was removed by filtration, and concentration was performed under reduced pressure. The reaction mixture was then purified by column chromatography using silica gel, to obtain 15.7 g of 1-(2-chloroethyl)-5-methoxyindole.

Workup

  1. customInto a flask of 500 ml capacity fitted with a stirrer
  2. temperaturecooling tube
  3. additionTo this mixture there was added dropwise
  4. additionAfter completion of the dropwise addition
  5. customthe ice-water bath was removed
  6. customreacted for 15 hours
  7. stirringwhile stirring
  8. temperatureheating
  9. temperatureunder reflux
  10. customAfter completion of the reaction
  11. customthe insoluble material was removed by filtration, and concentration
  12. customThe reaction mixture was then purified by column chromatography

Sources & evidence

ORD record
ord-31c149fbbaf546b18d0aa72ed2bb7eec
Source dataset
uspto-grants-2002_07
Patent number
US06416939B1

Reaction notes

Loading…