Acetone → HCID 13832256, compound

HRID 1381374Notes

Reaction equation

HRID 1381374 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](C2C(CCCO)OC(=O)C2=C)=[CH:4][CH:3]=1.[CH3:19][C:20]([CH3:22])=[O:21].OS(O)(=O)=O.O=[Cr](=O)=O.I([O-])(=O)(=O)=[O:33].[Na+].[C:38]([O:41]CC)(=[O:40])[CH3:39].C[C:45]([CH3:47])=[O:46]>O1CCOCC1.O.O=[Os](=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:19]2[CH:20]([CH2:22][CH2:39][C:38]([OH:41])=[O:40])[O:21][C:47](=[O:33])[C:45]=2[OH:46])=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 180AcetoneHCID 8857Ethyl AcetateHCID 23323871HCID 23323871, compoundHCID 23667635Sodium periodateHCID 131709961Jones' reagent

Product 1

HCID 13832256HCID 13832256, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

4-(4-Chlorophenyl)-5-(3-hydroxypropyl)-3-methylenetetrahydro-2-furanone (100 mg) was dissolved in acetone (2 ml), and Jones reagent (0.25 ml) was added dropwise with ice-cooling. The mixture was stirred at the same temperature for 2 hours, poured into ice water (20 ml) and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. The solvent was then distilled off to give crude 3-[3-(4-chlorophenyl)-5-oxo-4-methylenetetrahydro-2-furyl]propionic acid (80 mg) as an oil. The above compound was dissolved in dioxane (5 ml)-water (2 ml), and osmic acid (10 mg) was added. The mixture was stirred at room temperature for 5 minutes. To the reaction mixture was added portionwise sodium periodate (500 mg), and the mixture was stirred at the same temperature for 4 hours, followed by addition of water (20 ml) and extraction with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. The solvent was then distilled off and the residue was purified by preparative silica gel thin layer chromatography (developer: 10% methanol-chloroform) to give 3-[3-(4-chlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-2-furyl]propionic acid (20 mg) as colorless crystals.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was then distilled off
  6. customto give crude 3-[3-(4-chlorophenyl)-5-oxo-4-methylenetetrahydro-2-furyl]propionic acid (80 mg) as an oil
  7. additionwas added
  8. stirringThe mixture was stirred at room temperature for 5 minutes
  9. stirringthe mixture was stirred at the same temperature for 4 hours
  10. washThe extract was washed with water
  11. dry with materialdried over magnesium sulfate
  12. distillationThe solvent was then distilled off
  13. customthe residue was purified by preparative silica gel thin layer chromatography (developer: 10% methanol-chloroform)

Sources & evidence

ORD record
ord-395b2356b9e74e9585d46cfcf4df509e
Source dataset
uspto-grants-1986_04
Patent number
US04585789

Reaction notes

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