Ethyl acetate hexane → Pogostone

HRID 2229838Notes

Reaction equation

HRID 2229838 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10](=[O:16])[CH:11]=[CH:12][CH:13]([CH3:15])[CH3:14].[H][H].CCCCCC.C(OCC)(=O)C>C(OCC)(=O)C.[Pd]>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10](=[O:16])[CH2:11][CH2:12][CH:13]([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 1362314175169-81-3HCID 178418361HCID 178418361, compound

Product 1

HCID 54695756PogostoneYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Undernitrogen, 2.8 g of 4-hydroxy-6-methyl-3-(4-methyl-2-pentenoyl)-2-pyrone was dissolved in ethyl acetate and 0.14 g of 5% palladium/carbon was added thereto. The nitrogen in the reaction vessel was substituted by hydrogen and the reaction mixture was stirred at room temperature for 5 hours. After that, the reaction mixture was filtered through a Celite pad and the Celite pad was washed with 50 ml of ethyl acetate. The solution combined the filtrate with the washing solution was washed with 0.1% hydrochloric acid once, water twice and saturated brine once, subsequently. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue, which was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate =6/1) to give 2.68 g of 4-hydroxy-6-methyl-3-(4-methylpentanoyl)-2-pyrone.

Workup

  1. filtrationAfter that, the reaction mixture was filtered through a Celite pad
  2. washthe Celite pad was washed with 50 ml of ethyl acetate
  3. washwas washed with 0.1% hydrochloric acid once
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue, which

Sources & evidence

ORD record
ord-7620955616874d0fa271f86966ad5cd6
Source dataset
uspto-grants-2002_07
Patent number
US06420569B1

Reaction notes

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