Methyl iodide → 4-Methoxymethyl-1-tosylindole

HRID 1982467Notes

Reaction equation

HRID 1982467 reaction equation
[OH-].[K+].[CH3:3]I.[OH:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[S:16]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])(O)(=O)=O.C(Cl)Cl>[CH3:3][O:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[S:16]([C:19]1[CH:20]=[CH:21][C:22]([CH3:23])=[CH:24][CH:25]=1)(=[O:18])=[O:17]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 12553826[1-(4-Methylbenzene-1-sulfonyl)-1H-indol-4-yl]methanol

Product 1

HCID 131362764-Methoxymethyl-1-tosylindole

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

In sequence, 27 g of pulverulent potassium hydroxide, 27 ml of methyl iodide and 2.7 g of tetrabutyl-ammonium-hydrogen-sulfate are added to a solution of 13.5 g of 4-hydroxymethyl-1-tosylindole in 400 ml of methylene chloride. The substance is strongly agitated for 24 h. Then, it is filtered off of the potassium hydroxide, washed neutral with water, and the solvent is distilled off. The raw product (16.46 g) is crystallized out of diisopropylether. 12.2 g of 4-methoxymethyl-1-tosylindole with a m.p. of 85.5°-89° C. is obtained.

Workup

  1. filtrationThen, it is filtered off of the potassium hydroxide
  2. washwashed neutral with water
  3. distillationthe solvent is distilled off
  4. customThe raw product (16.46 g) is crystallized out of diisopropylether

Sources & evidence

ORD record
ord-d0602e11699041cc96576d60854ca5cd
Source dataset
uspto-grants-1986_06
Patent number
US04596808

Reaction notes

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