Methyl iodide → 4-Methoxymethyl-1-tosylindole

HRID 1903127Notes

Reaction equation

HRID 1903127 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

3rd stage: 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-5829b66794824e14a7b764835c0d7c28
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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