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1-Pyridin-3-yl-heptan-1-one synthesis

3synthesis methods
-

Yield:6294-61-7 78%

Reaction Conditions:

in tetrahydrofuran;hexane at -78; for 0.5 h;

Steps:



1 -Pyridin-3-yl-heptan-i -one. (compound 3, Scheme 1 ) ; 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 -780C under N2. After the addition, the resulting solution was stirred for 30 minutes at -780C. The mixture was allowed to warm to ambient temperature and poured into a NH4CI solution (10 g/50 ml H2O, O0C). 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, CDCI3) : δ 9.18 (d, J = 2 Hz, 1 H), 8.78 (d, J = 5 Hz, 2 Hz, 1 H), 8.24 (dt, J = 8 Hz, 2 Hz, 1 H), 7.47- 7.37 (m, 1 H), 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).

References:

WO2008/129054,2008,A2 Location in patent:Page/Page column 28-29