Acetic Acid → HCID 86678049, compound

Participants

Reaction Conditions

Reaction Steps

Diethylamine (30 g, 0.41 mol) and propargyl alcohol (18.4 g, 0.328 mol) are dissolved in 250 ml of toluene. 72.6 g of manganese dioxide (activated, <5 μm; 2.5 equiv.) are added portionwise while controlling the strong exotherm (temperature <50° C.) and the mixture is left stirring at 90° C. for 5 hours. The reaction mixture is filtered. The yellow filtrate is poured into a reactor surmounted by a Dean and Stark apparatus. 2-Ethylhexyl cyanoacetate (61.5 g, 0.312 mol) and catalyst (0.1 equiv., 1.77 ml of acetic acid and 3.2 ml of N,N-diethylamine) are added with stirring and the reaction mixture is brought to reflux. It is left at reflux for 5 hours 30 minutes. After cooling, 500 ml of dichloromethane are added and washing is carried out once with a saturated sodium bicarbonate solution and then twice with water. The organic phase is dried and then purified on a silica bed. The first fractions are recovered and concentrated under vacuum. 21.9 g (yield: 23%) of the pure fractions of the derivative of Example 5 are thus obtained in the form of an orange-coloured gum which crystallizes; recrystallization from heptane gave the derivative of Example 5 in the form of a yellow powder

Provenance & Evidence