Water → 2-Formyl-3-hydroxy-5-oxocyclopent-1-eneheptanoic acid
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]([OH:16])=[O:15])=[C:3]1[CH:17]=CC1C=CC=CC=1.I([O-])(=O)(=O)=[O:26].[Na+].O>O1CCOCC1.[Os](=O)(=O)(=O)=O>[CH:17]([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]([OH:16])=[O:15])=[O:26]Participants
Procedure
A mixture consisting of 13 parts of 3-hydroxy-5-oxo-2-styrylcyclopent-1-eneheptanoic acid, 17.8 parts of sodium periodate, 55 parts of water, 160 parts of dioxane and 2 parts of 2% osmium tetroxide in dioxane solution is stirred under nitrogen at room temperature for about 4 hours. That reaction mixture is then extracted with ether and the ether layer is separated and extracted several times with 0.5% aqueous sodium chloride. The salt extracts are saturated with sodium chloride, then extracted with ether. The ether layer is separated, dried over anhydrous sodium sulfate, concentrated and dried under reduced pressure to afford 2-formyl-3-hydroxy-5-oxocyclopent-1-eneheptanoic acid, characterized by an ultraviolet absorption maximum at about 228 millimicrons with a molecular extinction coefficient of about 10,100.
Workup
- extractionThat reaction mixture is then extracted with ether
- customthe ether layer is separated
- extractionextracted several times with 0.5% aqueous sodium chloride
- extractionextracted with ether
- customThe ether layer is separated
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-268b2419786a4d3d995db4e6c5b045bc
- Source dataset
- uspto-grants-1976_09
- Patent number
- US03980700
Reaction notes
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