Tetrahydrofuran → 1-(Pyridin-3-yl)heptan-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of anhydrous THF (15 ml) containing compound 2 (1.0 g, 6.02 mmol) was added 3.08 ml (7.66 mmol) of hexyl-lithium (2.5 M in hexane) dropwise at −78° C. under N2. After the addition, the resulting solution was stirred for 30 minutes at −78° C. The mixture was allowed to warm to ambient temperature and poured into a NH4Cl solution (10 g/50 ml H2O, 0° C.). Ethyl acetate was added and the organic layer was washed with a 5% NaHCO3 solution, dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography (diethyl ether/PE 1:1) to give compound 3 as an oil (0.91 g, 78%). 1H-NMR (200 MHz, CDCl3): δ 9.18 (d, J=2 Hz, 1H), 8.78 (d, J=5 Hz, 2 Hz, 1H), 8.24 (dt, J=8 Hz, 2 Hz, 1H), 7.47-7.37 (m, 1H), 2.99 (t, J=7 Hz, 2H), 1.84-1.65 (m, 2H), 1.47-1.25 (m, 6H), 0.90 (bt, J=7 Hz, 3H).

Provenance & Evidence