Diethyl Malonate → HCID 178470506, compound

Participants

Reaction Steps

Combine a solution of sodium ethoxide (5.5 mL, 21 wt % in ethanol) and diethyl malonate (2.50 mL, 16.5 mmol) in ethanol (26 mL) with a solution of 1-azidomethyl-3,5-bis-trifluoromethyl-benzene (4.40 g, 16.3 mmol) in ethanol (6 mL) and heat to 80° C. After 7 h, cool to RT and concentrate the mixture in vacuo. Dissolve the viscous oil in H2O (20 mL) and add aqueous 1N HCl until the solution reaches pH 2–3. Collect the white precipitate by filtration and dry under reduced pressure to give the title compound. MS (ES) 384.0 (M+H)+, MS (ES−) 382.1 (M−H); 1H NMR (400 MHz, CDCl3) δ 8.05 (s, 1H), 7.92 (s, 2H), 5.41 (s, 2H), 4.15 (q, 2H, J=7.3 Hz), 1.22 (t, 3H, J=7.3 Hz).

Provenance & Evidence