تفاعل #835904

معادلة التفاعل

1,5-diiodopentane

2-chloro-3-(4-chlorophenylsulfonylmethyl)pyridine

2-Chloro-3-(4-chlorophenylsulfonylmethyl)pyridine

butyl lithium

hexane

→

title compound

المردود 38.0%

2-Chloro-3-[1-(4-chlorophenylsulfonyl) cyclohexyl]pyridine

المردود 38.0%

المذيبات

dimethoxyethane

Water

ظروف التفاعل

المعالجة

1. 1
   أخرىAt −78° C.
2. 2
   أخرىwas gradually elevated to room temperature, at which
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITwas performed for 15 hours
5. 5
   استخلاصfollowed by extraction with ethyl acetate
6. 6
   غسيلThe organic layer was washed with brine
7. 7
   تجفيفdried over anhydrous sodium sulfate
8. 8
   ترشيحAfter filtration
9. 9
   تركيزthe filtrate was concentrated under reduced pressure
10. 10
    أخرىthe fraction obtained from the 15% ethyl acetate/hexane eluate
11. 11
    تركيزwas concentrated under reduced pressure
12. 12
    أخرىThe residue thus obtained
13. 13
    أخرىwas purified by high performance liquid chromatography (

الإجراء التجريبي

At −78° C., butyl lithium (a 1.57M hexane solution; 0.66 ml, 1.03 mmol) was added dropwise to a dimethoxyethane (5 ml) solution of the 2-chloro-3-(4-chlorophenylsulfonylmethyl)pyridine (156 mg, 0.516 mmol) obtained in Example 98. At −78° C., the resulting mixture was stirred for 20 minutes, followed by the addition of 1,5-diiodopentane (0.092 ml, 0.619 mmol). The temperature of the reaction mixture was gradually elevated to room temperature, at which stirring was performed for 15 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, and the fraction obtained from the 15% ethyl acetate/hexane eluate was concentrated under reduced pressure. The residue thus obtained was purified by high performance liquid chromatography (using a mixed solvent of water/acetonitrile/formic acid) to give the title compound (72 mg, 38%) 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.

المصدر