Toluene → Diisopropyl alpha-(4-hydroxy-3-methoxy-5-methylphenyl)-N-methyl-N-(3-picolyl)-aminomethylphosphonate

Participants

Reaction Steps

A mixture of 2.0 g (12 mmol) of 4-hydroxy-3-methoxy-5-methylbenzaldehyde, 1.8 g (13.2 mmol) of N-methyl-3-picolylamine and 2.2 g (13.2 mmol) diisopropyl phosphite dissolved in 15 ml toluene and a catalytic amount of p-toluenesulfonic acid (ca. 2 mg) contained in a flask connected to a Dean Stark apparatus was refluxed for 2 h. The solution was evaporated and the residue was purified by column chromatography (95/5 CHCl3/MeOH) to yield 2.1 g (40%) of a yellow oil.

Provenance & Evidence