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ChemicalBook CAS DataBase List 5-Hydroxyindole
1953-54-4

5-Hydroxyindole synthesis

9synthesis methods
-

Yield:1953-54-4 71%

Reaction Conditions:

with 1-N-ferrocenylmethyl benzimidazole tagged polymer in N,N-dimethyl-formamideReflux;

Steps:

Typical procedure for O-demethylation
General procedure: A mixture of aryl methyl ether (1 mmol) and [FemMerBenz]Al2Cl7 (200 mg, 0.96 mol %) in DMF (5 mL) was refluxed in an oil bath. After completion of the reaction as monitored by the TLC, the reaction mixture was cooled and filtered. The filtrate was poured into water (20 mL) and extracted with ethyl acetate (3 20 mL). The combined organic layers were dried over Na2SO4. Evaporation of the solvent followed by column chromatography over silica gel using ethyl acetate/ petroleum ether (1:4 v/v) afforded pure O-demethylated product, which was characterized by spectral methods.

References:

Kurane, Rajanikant;Gaikwad, Vipul;Jadhav, Jagannath;Salunkhe, Rajashri;Rashinkar, Gajanan [Tetrahedron Letters,2012,vol. 53,# 47,p. 6361 - 6366,6]

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