1-Iodoheptane → HCID 86746593, compound

Participants

Reaction Steps

A 50% oil dispersion of NaH (9.4 g) was washed three times with 20 ml of dry THF under argon and the remaining oil-free NaH was suspended in 600 ml of dry THF. cis-2-Butene-1,4-diol (50 ml, 46.7 g, 530 mmole) was then added slowly by syringe to the suspension. After a small amount of diol was added a gelatinous precipitate began to form, most of which went back into solution by the end of the addition. The mixture was allowed to stir for an additional hour and n-heptyliodide (30.4 ml, 42.0 g, 186 mmole) was added in one portion. The reaction was allowed to stir overnight. Aqueous NH4Cl was added to the mixture followed by 600 ml of ether. The organic layer was separated, washed with 200 ml of NaHCO3, 200 ml of brine, dried over MgSO4, filtered and the solvent evaporated to yield a pale yellow oil. Distillation afforded 23.82 g, bp 106°-10° C.(0.1 mm). 1H NMR δ5.76 (m, 2), 4.20 (t, 2, J=6 Hz), 4.04 (d, 2, J=6 Hz), 3.44 (t, 2, J=7 hz), 2.22 (t, 1, J=6 Hz), 1.59 (br t, 2, J=7 hz) 1.29 (br, 8), 0.88 (t, 3, J=7 hz).

Provenance & Evidence