1-Iodopropane → 2-Methyl-4-octyne

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methylpent-1-yne (0.588 mL, 5 mmol) in THF at −78° C. was added BuLi, 2.5 M in hexanes (2.200 mL, 5.50 mmol). After stirring 15 minutes at −78° C., the reaction mixture was allowed to warm to room temperature, 1-iodopropane (0.488 mL, 5.00 mmol) was added and the reaction mixture was stirred at rt for 3 days. The reaction mixture was quenched with water (50 mL) and the resulting mixture was transferred to a separatory funnel. The mixture was extracted with ether (75 mL). The organic layer was washed with brine (50 mL), dried (MgSO4) and concentrated to afford 2-methyloct-4-yne (555 mg, 4.47 mmol, 89% yield) as a light yellow liquid. 1H NMR (400 MHz, chloroform-d) δ ppm 0.91-0.99 (m, 9H) 1.45-1.53 (m, 2H) 1.70-1.81 (m, 1H) 2.03 (dt, J=6.5, 2.4 Hz, 2H) 2.12 (tt, J=7.0, 2.4 Hz, 2H).

Provenance & Evidence