Water → 1,1-Dimethylethyl 2-cyanobutanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of cyanoacetic acid tert-butyl ester (10.0 mL, 69.99 mmoL) (TCI America, Portland Oreg.) and DBU (10.5 mL, 69.99 mmol) in DMF (70 mL) was added iodoethane (6.8 mL, 84.00 mmol) dropwise at 0° C. The resulting mixture was heated to 70° C. for 20 hours. After cooling to room temperature, H2O (350 mL) and EtOAc (350 mL) were added. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-30% EtOAc/hexanes) to give the title compound in 5 g. 1H NMR (CDCl3, 200 MHz): δ=3.36 (dd, 1H, J=6.3 Hz and 6.3 Hz), 2.06-1.88 (m, 2H), 1.49 (s, 9H), 1.11 (t, 3H, J=7.3 Hz).

Provenance & Evidence