Iodine → (1E)-1-Iodo-1-octene

Participants

Reaction Steps

To a solution of oct-1-yne (113 mg, 1 mmol, available from Lancaster, Pelham, N.H., USA) and Cp2ZrCl2 (413 mg, 1.4 mmol, 1.4 eq.) in THF (4 mL) at RT was rapidly added a 1 M THF solution of LiAlH(Ot-Bu)3 (1.4 mL, 1.4 mmol, 1.4 eq.). A resulting dark red solution was stirred at RT for 15 min. Then, a solution of iodine (355 mg, 1.4 mmol, 1.4 eq., Aldrich) in THF (2 mL) was added. After additional stirring at RT for 15 min., the reaction mixture was quenched with 1 N HCl, and extracted with diethyl ether (3×10 mL). The organic extracts were combined and washed successively with saturated Na2SO3, H2O, and brine. The organic residue was then dried over MgSO4 and concentrated via evaporation under reduced pressure. Purification of the residue was performed using a short silica gel column (silica gel 60, 230-400 mesh) with EtOAc/hexanes as eluent. (E)-1-iodooct-1-ene (217 mg, 91% yield) was obtained as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm: 6.51 (dt, J=14.30, 7.12 Hz, 1H), 5.97 (d, J=14.31 Hz, 1H), 2.05 (dt, J=7.01, 6.96 Hz, 2H), 1.45-1.34 (m, 2H), 1.33-1.18 (m, 6H), 0.88 (t, J=6.66 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ ppm: 146.78, 74.21, 36.03, 31.56, 28.58, 28.32, 22.54, 14.04. The physical and spectral data are consistent with those previously reported (see Ren, H.; Krasovskiy, A.; Knochel, P. Org. Lett. 2004, 6, 4215-4217).

Provenance & Evidence