Methyl acetoacetate → sodium (2E)-4-methoxy4-oxo-2-buten-2-olate

HRID 890695Notes

Reaction equation

HRID 890695 reaction equation
[H-].[Na+:2].[C:3]([O:9][CH3:10])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].[H][H]>C1COCC1>[CH3:10][O:9][C:3](=[O:8])/[CH:4]=[C:5](/[O-:6])\[CH3:7].[Na+:2]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 24758Sodium hydride2×HCID 178418361HCID 178418361, compound

Product 1

HCID 23681258sodium (2E)-4-methoxy4-oxo-2-buten-2-olate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

60 g of a 30% strength sodium hydride suspension in mineral oil (744 mmol of NaH) are suspended in 250 ml of dry THF in an inert gas atmosphere. 86.4 g (744 mmol) of methyl acetoacetate in 200 ml of THF are slowly added dropwise, the resulting hydrogen being led directly into the waste air. After dropwise addition has taken place, the mixture is stirred at reflux for half an hour and then cooled. The solvent is stripped off in vacuo and the residual solid is washed with diethyl ether.

Workup

  1. additionAfter dropwise addition
  2. temperatureat reflux for half an hour
  3. temperaturecooled
  4. washthe residual solid is washed with diethyl ether

Sources & evidence

ORD record
ord-98ca9861945145df9681476471c7d59d
Source dataset
uspto-grants-2006_02
Patent number
US06998402B2

Reaction notes

Loading…