HCID 178418361, compound → HCID 178418595, compound

HRID 5260Notes

Reaction equation

HRID 5260 reaction equation
[OH:1][C:2]1[CH2:6][O:5][C:4](=[O:7])[C:3]=1[C:8](=[O:25])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1.[H][H]>C(OCC)(=O)C.[Pd]>[OH:1][C:2]1[CH2:6][O:5][C:4](=[O:7])[C:3]=1[C:8](=[O:25])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178418663HCID 178418663, compound

Product 1

HCID 178418595HCID 178418595, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.58 g (4.35 mmol) of 4-hydroxy-3-[10-(4-chlorophenyl)-1-oxodec-9-enyl]-2(5H)-furanone in 100 mL of ethyl acetate is added 250 mg of 5% palladium on carbon and subjected to atmospheric hydrogenation using a balloon to deliver the hydrogen. After 1.5 hours, the reaction is worked up by filtering through Solka Flok. The filtrate is washed with copious amounts of ethyl acetate and concentrated in vacuo to give 1.05 g (66%) of pure 4-hydroxy-3-[10-(4-chlorophenyl)1-oxodecyl]-2(5H)-furanone.

Workup

  1. filtrationby filtering through Solka Flok
  2. washThe filtrate is washed with copious amounts of ethyl acetate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44d7775ce6aa4fefbef4fb0336de5ad9
Source dataset
uspto-grants-1993_09
Patent number
US05242945

Reaction notes

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