2, 3-Dihydropyran is opened by hydrolysis in the presence of hydrochloric acid to afford 5-hydroxypentanal. According to Wittig reaction, 5-hydroxypentanal is reacted with potassium tert-butoxide and triethylphosphonoacetate in tetrahydrofuran to give...
2, 3-Dihydropyran is opened by hydrolysis in the presence of hydrochloric acid to afford 5-hydroxypentanal. According to Wittig reaction, 5-hydroxypentanal is reacted with potassium tert-butoxide and triethylphosphonoacetate in tetrahydrofuran to give ethyl 7-hydroxy-2-en-heptanoate.
And oxidation of the alcoholic group of that compound gives aldehyde(ethyl 7-oxo-2-en-heptanoate).
This aldelyde is reacted with hydroxylamine·hydrochloride in pyridine to make an oxime.
And this oxime is reacted with potassium carbonate or zinc chloride or pyridine in methylene chloride. But this intramolecular 1,3-dipolar cycloaddition of nitrone is not successful.
The structure of synthesized compounds was identified with IR and NMR spectra.