Ethyl 2-methylacetoacetate → Diethyl 2-acetyl-2-methyloctanedioate

HRID 1583074Notes

Reaction equation

HRID 1583074 reaction equation
[CH3:1][CH:2]([C:8]([CH3:10])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Br[CH:14](C)[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[C:24]1(C)C=CC=CC=1>>[C:8]([C:2]([CH3:24])([CH2:1][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:9])[CH3:10]

Participants

5

Reactant 4

HCID 701Ethyl 2-methylacetoacetateHCID 1140TolueneHCID 24758Sodium hydrideHCID 11499554HCID 11499554, compound

Product 1

HCID 22266834Diethyl 2-acetyl-2-methyloctanedioate

Procedure

Ethyl 2-methylacetoacetate (7.9 g, 60 mmol) was added to a stirred solution of 1.44 g of sodium hydride (60 mmol) in 80 mL of toluene over a 30 minutes period. The resulting solution was heated under reflux for two hours, cooled slightly and treated with ethyl 5-bromohexanoate over a 30 minutes period. The resulting mixture was then heated at reflux for twelve hours, cooled, and the solvent evaporated under reduced pressure. The residue, a yellow oil was used as such in the next step.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for two hours
  3. temperaturecooled slightly
  4. temperatureThe resulting mixture was then heated
  5. temperatureat reflux for twelve hours
  6. temperaturecooled
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-97e0e1de9f6344aeba2d638adaf1902e
Source dataset
uspto-grants-2004_05
Patent number
US06740755B2

Reaction notes

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