Diethyl Malonate → 1,3-Diethyl 2-[[2-(trifluoromethyl)phenyl]methyl]propanedioate

HRID 326702Notes

Reaction equation

HRID 326702 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CC[O-].[Na+].[F:16][C:17]([F:27])([F:26])[C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Br>C(O)C>[F:16][C:17]([F:26])([F:27])[C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 2723922Sodium ethoxide

Product 1

HCID 537090431,3-Diethyl 2-[[2-(trifluoromethyl)phenyl]methyl]propanedioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

40 ml of diethyl malonate in 350 ml of ethyl alcohol were treated portionwise with 18.6 g of sodium ethylate at room temperature and the mixture was then treated with 12 g of o-trifluoromethylbenzyl bromide within 30 minutes. The reaction mixture was stirred at room temperature overnight. The alcohol was distilled under reduced pressure and the residue was dissolved in ethyl acetate. The solution was washed twice with water and once with NaCl solution, dried under reduced pressure and evaporated. The residue was chromatographed over 300 g of SiO2 with CH2Cl2 /AcOEt 95:5 and yielded 11 g of diethyl [o-(trifluoromethyl)benzyl]malonate as a colourless oil.

Workup

  1. distillationThe alcohol was distilled under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed twice with water and once with NaCl solution
  4. customdried under reduced pressure
  5. customevaporated
  6. customThe residue was chromatographed over 300 g of SiO2 with CH2Cl2 /AcOEt 95:5

Sources & evidence

ORD record
ord-88cc38360f2b4e2195fabb4351afbdb9
Source dataset
uspto-grants-1993_12
Patent number
US05270313

Reaction notes

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