Sodium periodate → HCID 21512315, compound

Participants

Reaction Steps

A convenient procedure for manufacture of the 2-formyl compounds consists of cleaving the glycol structure of the corresponding 2-(α,β-dihydroxyphenethyl) substances. 3-Acetoxy-5-oxo-2-(α,β-dihydroxyphenethyl)cyclopent- 1-eneheptanoate in ethanol is contacted with aqueous sodium periodate, thus affording 3-acetoxy-2-formyl-5-oxocyclopent-1-eneheptanoate. The 2-formyl compounds are alternatively produced from the corresponding 2-styryl derivatives by combining the hydroxylation and cleavage processes. Methyl 3-hydroxy-5-oxo-2-styrylcyclopent- 1-eneheptanoate in aqueous dioxane is thus allowed to react with osmium tetroxide and sodium periodate to afford methyl 2-formyl-3-hydroxy-5-oxocyclopent-1-eneheptanoate.

Provenance & Evidence