Acetone → 1,3-Butanedione, 1-(2-furanyl)-

HRID 1780958

Reaction equation

HRID 1780958 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8]C)=O.[H-].[Na+].[CH3:12][C:13]([CH3:15])=[O:14].Cl>C(OCC)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH2:12][C:13](=[O:14])[CH3:15])=[O:8]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 11902Methyl 2-furoateHCID 24758Sodium hydride

Product 1

HCID 121681,3-Butanedione, 1-(2-furanyl)-Yield 99.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4.27 ml (5.04 g, 40 mmol) methyl 2-furoate was added to a suspension of NaH (made from 3.83 g commercial NaH slurry by removal of the mineral oil with pentane) in 30 ml anhydrous diethyl ether. To this was added, so as to maintain the temperature below 30° C., 5.87 ml (4.64 g, 80 mmol) acetone (dried over CaCl2). This mixture was heated under reflux for 2 h, cooled, and divided between diethyl ether and 3M HCl. The ether layer was washed with brine, dried (MgSO4), and concentrated to yield 6.06 g of a red oil (raw yield 99%) which was purified by vacuum distillation (b.p. 85°-90° C./1 torr).

Workup

  1. custommade from 3.83 g commercial NaH slurry by removal of the mineral oil with pentane) in 30 ml anhydrous diethyl ether
  2. additionTo this was added
  3. temperatureThis mixture was heated
  4. temperatureunder reflux for 2 h
  5. temperaturecooled
  6. washThe ether layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8c764efa47ef4b9b8b9f366061dd03f4
Source dataset
uspto-grants-1997_05
Patent number
US05631374

Linked notes

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