Sodium periodate → HCID 21512315, compound

HRID 1580248Notes

Reaction equation

HRID 1580248 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:3]1[CH:18]=CC1C=CC=CC=1.I([O-])(=O)(=O)=[O:27].[Na+]>O1CCOCC1.[Os](=O)(=O)(=O)=O>[CH:18]([C:3]1[CH:2]([OH:1])[CH2:6][C:5](=[O:7])[C:4]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:27]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 68136775HCID 68136775, compound

Product 1

HCID 21512315HCID 21512315, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

The 2-formyl compounds useful in this invention are then conveniently prepared by cleaving the glycol structure of the corresponding 2-(α,β-dihydroxyphenethyl) substances. Methyl 3-hydroxy-5-oxo-2-(αβ-dihydroxyphenethyl)cyclopent-1-eneheptanoate in ethanol is contacted with aqueous sodium periodate, thus affording methyl 3-hydroxy-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.

Sources & evidence

ORD record
ord-3a8bda30869942169149dfa416a0c0d7
Source dataset
uspto-grants-1976_01
Patent number
US03932467

Reaction notes

Loading…