Ethyl Acetate → HCID 22731438, compound

HRID 1356734Notes

Reaction equation

HRID 1356734 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][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[NH4+].[Cl-]>C(OCC)C.[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][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 22731420HCID 22731420, compound

Product 1

HCID 22731438HCID 22731438, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

Under cooling with ice, a solution of methyl ester of 5-tert-butyl-4-tert-butyldimethylsilanyloxymethylfuran-2-carboxylic acid (2.16 g, 6.63 mmol) in diethyl ether (20 ml) was added to a suspension of lithium aluminum hydride (503 mg, 13.3 mmol) in diethyl ether (20 ml), followed by stirring for 1 hour. Under cooling with ice, the mixture was mixed with ethyl acetate and saturated aqueous NH4Cl and filtered. The filtrate was extracted with ethyl acetate and 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 (80 ml), mixed with manganese dioxide (5.76 g, 66.3 mmol) and stirred overnight. After filtering the reaction mixture, the filtrate was evaporated to remove the solvent to give the titled compound (1.58 g, 81%).

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 (80 ml)
  10. stirringstirred overnight
  11. filtrationAfter filtering the reaction mixture
  12. customthe filtrate was evaporated
  13. customto remove the solvent

Sources & evidence

ORD record
ord-784391b543824e6a9b915e5212e037b3
Source dataset
uspto-grants-2003_07
Patent number
US06586630B1

Reaction notes

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