3-Methyl-2-butanone → 1-methoxy-5-methylhexane-2,4-dione

HRID 2071046Notes

Reaction equation

HRID 2071046 reaction equation
[H-].[Na+].C[O:4][CH2:5][C:6]([O:8][CH3:9])=O.[CH3:10][CH:11]([CH3:15])[C:12](=[O:14])[CH3:13]>CCOCC>[CH3:9][O:8][CH2:6][C:5](=[O:4])[CH2:13][C:12](=[O:14])[CH:11]([CH3:15])[CH3:10]

Participants

5

Reactant 3

HCID 112513-Methyl-2-butanoneHCID 24758Sodium hydrideHCID 80507Methyl methoxyacetate

Product 1

HCID 100121541-methoxy-5-methylhexane-2,4-dioneYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred slurry of NaH (1.02 g, 26 mmol, washed with anhydrous hexanes) in ether (10 mL) was added methyl methoxyacetate (2.3 mL, 23 mmol) followed by 3-methyl-2-butanone (2.4 mL, 23 mmol) in ether (5 mL). The resulting mixture was stirred for 15 h and became a clear yellow solution. The reaction was quenched with saturated aqueous NH4Cl. The resulting mixture was extracted with EtOAc (2×20 mL). The combined organic layer was washed with H2O, brine, dried with Na2SO4 and concentrated under reduced pressure to provide 1-methoxy-5-methylhexane-2,4-dione (2.90 g, 80%) as a mixture of keto and enol form.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionThe resulting mixture was extracted with EtOAc (2×20 mL)
  3. washThe combined organic layer was washed with H2O, brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea82e82546a1470b83d2ef3cc773b77c
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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