Toluene → HCID 136404656, compound

Participants

Reaction Steps

A solution of 2.5 g (13.7 mmol) syringaldehyde and 1.6 g (14.4 mmol) 4-picolylamine dissolved in 100 ml toluene contained in a flask connected to a Dean-Stark apparatus was refluxed for 3 h. Toluene was evaporated under vacuum then the residue dissolved in 10 ml THF was heated with 5.1 g (36.8 mmol) diethyl phosphite for 6 h. THF was evaporated and the residue was purified by column chromatography (SiO2, 95/5 CHCl3/MeOH). Recrystallisation in a mixture of CH2Cl2-petroleum ether gave 3.7 g (45%) of a solid, mp=124-126° C.

Provenance & Evidence