Methyl Ethyl Ketone → Phenylmethoxy-2,4-hexandione

HRID 1656029Notes

Reaction equation

HRID 1656029 reaction equation
[CH3:1][C:2](=[O:5])[CH2:3][CH3:4].C([N-]C(C)C)(C)C.[Li+].[CH2:14]([O:21][CH2:22][C:23]([O:25]C)=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[C:15]1([CH2:14][O:21][CH2:22][C:23](=[O:25])[CH2:1][C:2](=[O:5])[CH2:3][CH3:4])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 2724682Lithium diisopropylamideHCID 11745225Methyl 2-(benzyloxy)acetate

Product 1

HCID 20093386Phenylmethoxy-2,4-hexandione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Butanone (32.7 ml) in dry THF (120 ml) was added to lithium diisopropylamide (1.5M in THF; 250 ml) at -78° C. Methyl benzyloxyacetate (30,0 g) was added with stirring and the mixture allowed to warm to room temperature and was then heated at 45° overnight. After cooling the reaction was quenched with saturated ammonium chloride solution, acidified and extracted with ether (3×100 ml). After drying and evaporation, the title compound was obtained as a brown oil (45.6 g).

Workup

  1. temperaturewas then heated at 45° overnight
  2. temperatureAfter cooling the reaction
  3. customwas quenched with saturated ammonium chloride solution
  4. extractionextracted with ether (3×100 ml)
  5. customAfter drying
  6. customevaporation

Sources & evidence

ORD record
ord-4c853efd49084a42b657fdfc8d4a507a
Source dataset
uspto-grants-1993_10
Patent number
US05252593

Reaction notes

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