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

Participants

Reaction Steps

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.

Provenance & Evidence