Diethyl phenylmalonate → Diethyl 2-phenyl-2-(2-methyl-2-propenyl)malonate

HRID 902744Notes

Reaction equation

HRID 902744 reaction equation
[C:1]1([CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][C:19](=[CH2:22])[CH2:20]Br>CN(C=O)C.O>[C:1]1([C:7]([CH2:20][C:19]([CH3:22])=[CH2:18])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 66514Diethyl phenylmalonateHCID 3577853-Bromo-2-methyl-1-propene

Product 1

HCID 69251454Diethyl 2-phenyl-2-(2-methyl-2-propenyl)malonateYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

NaH (440 mg of a 60% dispersion in mineral oil, 11 mmole) was washed free of mineral oil, and suspended in 20 mL of DMF. This was treated with a solution of diethyl phenylmalonate (2.36 g, 10 mmole) in 10 mL of DMF, and the reaction was stirred for 15 minutes, at which time the solution was clear. 2-Methylallyl bromide (2.0 mL) was added, and stirring continued for 1 hour. The reaction was diluted with H2O and extracted with Et2O. The extracts were washed with H2O, dried and the solvent removed and gave the titled compound, 2.85 g (95% yield). MS (ESI) 291 (MH+)

Workup

  1. washNaH (440 mg of a 60% dispersion in mineral oil, 11 mmole) was washed free of mineral oil
  2. stirringstirring
  3. waitcontinued for 1 hour
  4. extractionextracted with Et2O
  5. washThe extracts were washed with H2O
  6. customdried
  7. customthe solvent removed

Sources & evidence

ORD record
ord-2527cfe60a1e497caa19715798cda403
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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