Sodium → 4-Methoxymethyl-indole

HRID 1982468Notes

Reaction equation

HRID 1982468 reaction equation
[Na].[CH3:2][O:3][CH2:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2S(C1C=CC(C)=CC=1)(=O)=O>C(O)C>[CH3:2][O:3][CH2:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2

Participants

4

Reactant 2

HCID 5360545SodiumHCID 131362764-Methoxymethyl-1-tosylindole

Product 1

HCID 129091524-Methoxymethyl-indoleYield 77.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2.84 g of sodium in 155 ml of ethanol is dripped within 10 minutes into a solution of 15.57 g of 4-methoxymethyl-1-tosylindole in 155 ml of ethanol, whereupon the mixture is heated with reflux for 11/2 h; next it is cooled, stirred into 1.5 liters of half-saturated ice-cold sodium-di-hydrogen-phosphate solution, extracted with ethyl acetate; whereupon, the ethyl-acetate extracts are washed neutral with water. After the solvent has been distilled off, the raw product is chromatographed on silical gel with hexane/ethyl-acetate (0-20%). 6.2 g of 4-methoxymethyl-indole is obtained in the form of a colorless oil.

Workup

  1. temperatureis heated
  2. temperaturewith reflux for 11/2 h
  3. temperaturenext it is cooled
  4. extractionextracted with ethyl acetate
  5. washwhereupon, the ethyl-acetate extracts are washed neutral with water
  6. distillationAfter the solvent has been distilled off
  7. customthe raw product is chromatographed on silical gel with hexane/ethyl-acetate (0-20%)

Sources & evidence

ORD record
ord-e690d7444e3b44d2b0d67a34f5254e63
Source dataset
uspto-grants-1986_06
Patent number
US04596808

Reaction notes

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