Water → HCID 21512315, compound

HRID 1580252Notes

Reaction equation

HRID 1580252 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+].O>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

6

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 68136775HCID 68136775, compound

Product 1

HCID 21512315HCID 21512315, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 13.5 parts of dl-methyl 3-hydroxy-5-oxo-2-styrylcyclopent-1-eneheptanoate, 17.8 parts of sodium periodate, 55 parts of water, 160 parts of dioxane and 2 parts by volume of a 2% osmium tetroxide in dioxane solution is stirred at room temperature under nitrogen for about 4 hours. The reaction mixture is extracted with ether and the ether solution is dried over anhydrous sodium sulfate, then concentrated to dryness under reduced pressure. The resulting residue is purified by dry column chromatography on silica gel containing 8% of water, using 50% ethyl acetate in benzene, thus affording dl-methyl 2-formyl-3-hydroxy-5-oxocyclopent-1-eneheptanoate, characterized by an ultraviolet absorption maximum at about 228 millimicrons with a molecular extinction coefficient of about 10,200.

Workup

  1. extractionThe reaction mixture is extracted with ether
  2. dry with materialthe ether solution is dried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe resulting residue is purified
  5. dry with materialby dry column chromatography on silica gel containing 8% of water

Sources & evidence

ORD record
ord-e17bda957807420c8744c4dedc11ba21
Source dataset
uspto-grants-1976_01
Patent number
US03932467

Reaction notes

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