[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol → 2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde

Participants

Reaction Steps

In analogy to the procedures described in examples 8A] and 31B], 3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester (example 60B]) was reacted with [rac]-3-(1-chloro-3-methyl-butyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine (prepared from [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol (example 1M]) by i) oxidation with MnO2 in analogy to the procedure described in example 3A] to yield 2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde; ii) treatment with isobutyl magnesium chloride and iii) reaction with SOCl2 in analogy the procedures described in examples 4A] and 4B]) to give [rac]-3-(2-methyl-4-{3-methyl-1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-butoxy}-phenyl)-propionic acid ethyl ester, which was subsequently saponified to yield the title compound as light yellow solid.

Provenance & Evidence