Diethyl Malonate → HCID 594682, compound

HRID 1458955Notes

Reaction equation

HRID 1458955 reaction equation
CC[O-].[Na+].[Na].[C:6]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].Br[CH2:18][CH2:19][CH:20]=[CH2:21]>CCO>[CH2:21]([CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]([O:14][CH2:15][CH3:16])=[O:13])[CH2:20][CH:19]=[CH2:18]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 21241Homoallyl bromideHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 594682HCID 594682, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of NaOEt, prepared from the treatment of 1 L EtOH with sodium metal (19.5 g, 0.813 mol), was cooled to 0° C. and diethyl malonate (3-1, 100 g, 0.625 mol) was added dropwise over 0.5 h. After the addition was complete, the reaction was stirred for an additional 0.5 h, then a solution of 1-bromo-3-butene (76.1 mL, 0.75 mol) in 100 mL EtOH was added dropwise over forty-five minutes. The reaction was heated to reflux for 18 h, cooled and the solvent was removed in vacuo. The residue was dissolved in H2O and washed with EtOAc. The organic layer was dried with brine and MgSO4, filtered and evaporated. Fractional distillation of the residue (0.25-0.4 mm Hg, 70°-80° C.) gave 3-2 as a clear liquid.

Workup

  1. additionAfter the addition
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 18 h
  4. temperaturecooled
  5. customthe solvent was removed in vacuo
  6. dissolutionThe residue was dissolved in H2O
  7. washwashed with EtOAc
  8. dry with materialThe organic layer was dried with brine and MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. distillationFractional distillation of the residue (0.25-0.4 mm Hg, 70°-80° C.)

Sources & evidence

ORD record
ord-a600ad4f0efe48a592ff38be423e3ff1
Source dataset
uspto-grants-1998_12
Patent number
US05852045

Reaction notes

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