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

HRID 2210674Notes

Reaction equation

HRID 2210674 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-90d4868ad6d54944a8219d9dbc7f186a
Source dataset
uspto-grants-1995_10
Patent number
US05459272

Reaction notes

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