Sodium Iodide → Ethyl 1-(4-iodobutyl)-1-cyclobutanecarboxylate

Participants

Reaction Steps

To a solution of ethyl 1-(4-chlorobutyl)-1-cyclobutanecarboxylate (21.21 g, 97.0 mmol) in 2-butanone (125 mL) was added NaI (19.07 g, 127 mmol). The reaction mixture was stirred under reflux for 20 h and diluted with Et2O (500 mL). The resulting mixture was washed with aqueous Na2S2O3 (10% (w/w), 250 mL), brine (250 mL), dried (Na2SO4) and evaporated in vacuo to give ethyl 1-(4-iodobutyl)-1-cyclobutanecarboxylate (29.91 g, 99%) as a slightly yellow oil. 1H NMR (CDCl3): δ=4.14 (q, J=7.1 Hz, 2H), 3.17 (t, J=6.9 Hz, 2H), 2.49-2.32 (m, 2H), 1.98-1.69 (m, 8H), 1.37-1.19 (m, 2H), 1.27 (t, J=7.1 Hz, 3H). 13C NMR (CDCl3): δ=176.5, 60.3, 47.5, 36.9, 33.7, 30.1 (2×), 26.0, 15.7, 14.5, 6.8. HRMS calcd for C11H20IO2 (MH+): 311.0508, found: 311.0511.

Provenance & Evidence