Hexane → 4-[1-(4-Chlorophenylsulfonyl)pentyl]pyridine

Temperature

-78 °C

At −78° C., butyl lithium (a 1.57M hexane solution; 0.29 ml, 0.448 mmol) was added dropwise to a tetrahydrofuran (5 ml) solution of 4-(4-chlorophenylsulfonylmethyl)pyridine (100 mg, 0.374 mmol). At −78° C., the resulting mixture was stirred for 10 minutes. Iodobutane (51 μl, 0.448 mmol) was then added thereto. The temperature of the reaction mixture was gradually elevated to room temperature, at which stirring was performed for 16 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column. The fraction obtained from the hexane:ethyl acetate (=2:1) eluate was concentrated under reduced pressure to give the title compound (76 mg, 63%) as a white solid. The resulting solid was washed with hexane-ether and then collected by filtration, whereby the title compound was obtained as a white powder.

1. customAt −78° C.
2. customwas gradually elevated to room temperature, at which
3. stirringstirring
4. waitwas performed for 16 hours
5. extractionfollowed by extraction with ethyl acetate
6. washThe organic layer was washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationAfter filtration
9. concentrationthe filtrate was concentrated under reduced pressure
10. customThe fraction obtained from the hexane
11. concentrationethyl acetate (=2:1) eluate was concentrated under reduced pressure

ORD record

ord-48108732bb5a4d088ae621ee67d288b9

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399775B2