Oxygen → 3-Ethyl-2,4-pentanediol

HRID 132719Notes

Reaction equation

HRID 132719 reaction equation
O=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:9]([CH:11]([C:15](=[O:17])[CH3:16])[C:12](=[O:14])[CH3:13])[CH3:10].[OH-].[Na+]>N#N.C1COCC1.O>[CH2:9]([CH:11]([CH:15]([OH:17])[CH3:16])[CH:12]([OH:14])[CH3:13])[CH3:10]

Participants

8

Reactant 4

HCID 977OxygenHCID 14798Sodium HydroxideHCID 737613-Ethylpentane-2,4-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 218678653-Ethyl-2,4-pentanediolYield 64.3%

Reagents, catalysts & solvents 3

HCID 947NitrogenSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In N2 atmosphere free of water and oxygen, to a reactor were successively added 0.024 mol LiAlH4 and 100 ml THF, followed by adding dropwise 0.04 mol 3-ethyl-2,4-pentandione while cooling the mixture with ice-bath. The reaction was allowed to continue at room temperature for 48 hours. Aqueous solution of sodium hydroxide was added carefully to stop the reaction. The reaction mixture was filtered and the cake was washed with anhydrous ethyl ether for three times. The organic phase was combined and dried over anhydrous sodium sulfate. Removing the solvent gave 3.4 g product.

Workup

  1. temperaturewhile cooling the mixture with ice-bath
  2. customthe reaction
  3. filtrationThe reaction mixture was filtered
  4. washthe cake was washed with anhydrous ethyl ether for three times
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoving the solvent

Sources & evidence

ORD record
ord-10f2cc159f3e4c45981540408442cd7c
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Reaction notes

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