Ethanol → HCID 81689729, compound

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:

1. temperatureThe mixture was heated
2. temperatureunder reflux for 2 h
3. customThe ethanol was removed under reduced pressure and dichloromethane (100 mL)
4. additionwas added
5. extractionThe dichloromethane was extracted with 5% HCl (100 mL) and water (100 mL)
6. dry with materialThe dichloromethane was dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe remaining orange oil (1.94 g) was purified on silica gel (100 g)
10. washeluting with 10-30% ethyl acetate in heptanes

ORD record

ord-0599962b3d9b436fa662b26ac8445481

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09364465B2