Ethanol → HCID 81689729, compound

Participants

Reaction Steps

DHA aldehyde from Part C (1.50 g, 4.8 mmol) was dissolved in ethanol (30 mL) with thiazolidine-2,4-dione (0.81 g, 6.8 mmol), and a catalytic amount of piperidine (103 mg, 1.2 mmol). The mixture was heated under reflux for 2 h. The heat was turned off and the solution slowly cooled to RT over 1.5 h. The ethanol was removed under reduced pressure and dichloromethane (100 mL) was added. The dichloromethane was extracted with 5% HCl (100 mL) and water (100 mL). The dichloromethane was dried over sodium sulfate, filtered, and concentrated. The remaining orange oil (1.94 g) was purified on silica gel (100 g), eluting with 10-30% ethyl acetate in heptanes. The experiment produced DHA-TZ olefin intermediate (4 in Scheme 2) (1.45 g, 74% yield, purity 85-90% by NMR) as a light yellow oil and is further characterized by:

Provenance & Evidence