Diethyl Malonate → Diethyl 4-t-Butyl-benzoylmalonate

HRID 1740071Notes

Reaction equation

HRID 1740071 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:14]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[H-].[Na+].[Cl-].[NH4+]>O1CCCC1>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:14]([O:22][CH2:23][CH3:24])=[O:21])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 743724-tert-Butylbenzoyl chloride

Product 1

HCID 21837646Diethyl 4-t-Butyl-benzoylmalonateYield 87.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 25.3 g of 4-t-butyl-benzoyl chloride, 30.9 g of diethyl malonate and 500 ml of tetrahydrofuran was stirred under cooling with ice and then stirred with 5.9 g of 55% sodium hydride for another 1 hour. To the reaction solution, 200 ml of aqueous ammonium chloride was added, and the tetrahydrofuran was removed by evaporation under reduced pressure. The residue was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 36.2 g of the title compound as a pale yellow oily substance.

Workup

  1. temperatureunder cooling with ice
  2. customthe tetrahydrofuran was removed by evaporation under reduced pressure
  3. extractionThe residue was extracted with chloroform
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-66955c41bdf249b7b93156a7a25277fe
Source dataset
uspto-grants-1999_10
Patent number
US05968967

Reaction notes

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