4-Toluenesulfonyl chloride → 1-tosyl-3-acetylpyrrole

Participants

Reaction Steps

The synthesis of 1-(N-tosyl)-3-(hydroxyethyl)pyrrole was carried out as described by Korri-Youssoufi et al., Materials Science and Engineering C15 (2001) 265-268. In a first step, 1-(N-tosyl) pyrrole was synthesized from pyrrole using tosyl chloride in the presence of a strong base, potassium tert-butoxide. Next, acylation of the 1-(N-tosyl)pyrrole with acetic anhydride made it possible to obtain 1-tosyl-3-acetylpyrrole, which was converted to methyl 2-[3-(1-N-tosylpyrrole)]acetate by oxidative transposition, using thallium nitrate in the presence of montmorillonite. Reduction under mild conditions with borane dimethyl sulfide gave the desired product, 1-(N-tosyl)-3-(hydroxyethyl)pyrrole. The overall yield of the reaction was 21.8%.

Provenance & Evidence