1-Iodopropane → 2-Methyl-4-octyne

Temperature

-78 °C

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).

1. temperatureto warm to room temperature
2. stirringthe reaction mixture was stirred at rt for 3 days
3. customThe reaction mixture was quenched with water (50 mL)
4. customthe resulting mixture was transferred to a separatory funnel
5. extractionThe mixture was extracted with ether (75 mL)
6. washThe organic layer was washed with brine (50 mL)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated

ORD record

ord-a98154d7b67848caba2cddd82f7824a6

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354398B2