Formation of oxime and isoxazoline from aldehyde derivatives via one-pot synthesis

Abstract

Isoxazolines and isoxazoles are used as intermediates to create important functional groups. They also have practical uses such as the products soretolide, an epileptic seizure medication, valdecoxib, an anti-inflammatory drug, muscimol, a GABA receptor, and isoxaflutole, a pesticide. Finding a one-pot synthesis to produce isoxazoline from an aldehyde will be time and resource efficient. The one-pot synthesis then can be used for when doing a synthesis with an isoxazoline as an intermediate or just to make isoxazoline products. The most successful type of aldehyde used to make isoxazoline using one-pot synthesis is aromatic aldehydes without an alcohol group. The specific aldehydes that were tested are anisaldehyde, 3,4,5- trimethoxybenzaldehyde, and 3-nitrobenzaldehyde. The reactants used are hydroxylamine hydrochloride, 10% sodium hydroxide, ethanol, water, allyl alcohol, bleach, and dichloromethane. Aliphatic aldehydes like heptaldehyde and butrylaldehyde were also tested. The only change in the procedure when using aliphatic aldehydes is using 50% sodium hydroxide instead of 10% sodium hydroxide. Even though this procedure would make isoxazoline, there was a large amount of impurities with little isoxazoline. Further research would need to be done to find a better procedure to make more isoxazoline.