Sulfuric Acid → HCID 178448151, compound

Participants

Reaction Steps

A solution of 1.51 g of 6-(4-fluorophenyl)-3-pyridinecarboxaldehyde and 1.10 g of 2-propyl-1,3-propanediol in 50 ml of toluene was treated with 10 drops of 10 percent (v/v) sulphuric acid. The mixture was heated to boiling for 1.5 hours, whereby moist toluene was distilled off and replaced by fresh toluene. Then, the reaction mixture was neutralized with triethylamine and, after cooling, washed three times with water, dried over sodium sulphate and concentrated. Chromatographic purification of the residue on 60 g of silica gel with toluene/acetone (vol. 99:1) and two-fold recrystallization of the trans/cis mixture from hexane/ethyl acetate (vol. 1:1) gave 0.51 g of pure 5-(trans-5-propyl-1,3-dioxan-2-yl)-2-(4-fluorophenyl)pyridine; m.p. (C-SA) 106.5° C., SA -N 117.5° C., cl.p. (N-I) 163° C.

Provenance & Evidence