Methyl iodide → HCID 67515742, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (60% in oil, 0.8 g, 19 mmol) in DMF (50 mL) was added tert-butyl ethyl (2-methyl-6-nitropyridin-3-yl)propanedioate (4 g, 13 mmol) at room temperature. The mixture was stirred for 1 hour and CH3I (3.7 g, 26 mmol) was added. The mixture was heated to 40° C. for 2 hours. Cooled to ambient temperature, the mixtue was poured to ice/water, extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatograph silca gel to give tert-butyl ethyl rnethyl(2-methyl-6-nitropyridin-3-yl)propanedioate. 1H-NMR (400 MHz, CDCl3) δ 8.01 (d, J=8.6 Hz, 1H), 7.79 (d, J=8.6 Hz, 1H), 4.19-4.27 (m, 2H), 2.59 (s, 3H), 1.85 (s, 3H), 1.45 (s, 9H), 1.28 (t, J=7.0 Hz, 3H).

Provenance & Evidence