2-(1-benzyl-2-hydroxymethyl-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol → 1-benzyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-1H-indole-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.03 g (2.56 mmol) of 2-(1-benzyl-2-hydroxymethyl-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (example 41) in 10 mL toluene were added 2.22 g (25.6 mmol) of MnO2 powder. The mixture was stirred at 80° C. overnight. Filtration through decalite, evaporation of the solvent and column chromatography on silica gel with n-heptane/EtOAc 3:1 yielded 0.342 g (33%) of 1-benzyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-1H-indole-2-carbaldehyde, MS: 400 (M−H)−.

Provenance & Evidence