Ethyl Acetate → HCID 88038328, compound

HRID 1356727Notes

Reaction equation

HRID 1356727 reaction equation
[C:1]([C:5]1[O:9][C:8]([C:10](O)=[O:11])=[CH:7][C:6]=1[CH2:13][O:14][CH2:15][O:16][CH3:17])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[NH4+].[Cl-]>C1COCC1.[O-2].[O-2].[Mn+4]>[C:1]([C:5]1[O:9][C:8]([CH:10]=[O:11])=[CH:7][C:6]=1[CH2:13][O:14][CH2:15][O:16][CH3:17])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 22731411HCID 22731411, compound

Product 1

HCID 88038328HCID 88038328, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Under cooling with ice, a solution of methyl ester of 5-tert-butyl-4-methoxymethoxymethylfuran-2-carboxylic acid (490 mg, 1.91 mmol) in THF (10 ml) was added to a suspension of lithium aluminum hydride (145 mg, 3.82 mmol) in THF (10 ml), followed by stirring for 1 hour. Under cooling with ice, the mixture was mixed with ethyl acetate and saturated aqueous NH4Cl, filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate and evaporated to remove the solvent. The thus obtained residue was dissolved in methylene chloride (20 ml) and mixed with manganese dioxide (2.49 g, 28.7 mmol), followed by stirring for 1 day. The reaction mixture was filtered and the filtrate was evaporated to remove the solvent; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:4) to give the titled compound (379 mg, 88%).

Workup

  1. temperatureUnder cooling with ice
  2. temperatureUnder cooling with ice
  3. filtrationfiltered
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customto remove the solvent
  9. dissolutionThe thus obtained residue was dissolved in methylene chloride (20 ml)
  10. stirringby stirring for 1 day
  11. filtrationThe reaction mixture was filtered
  12. customthe filtrate was evaporated
  13. customto remove the solvent

Sources & evidence

ORD record
ord-f330ac54c8114686b500c379dbfb7b5f
Source dataset
uspto-grants-2003_07
Patent number
US06586630B1

Reaction notes

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