Hexane → 2-Chloro-3-[1-(4-chlorophenylsulfonyl)cycloheptyl]pyridine

HRID 748721

反応式

HRID 748721 の反応式
C([Li])CCC.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[Cl:12][C:13]1[C:18]([CH2:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:17][CH:16]=[CH:15][N:14]=1.ICCCCCCI>O.C(COC)OC>[Cl:12][C:13]1[C:18]([C:19]2([S:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:17][CH:16]=[CH:15][N:14]=1

参加物

7

反応物 4

HCID 8058HexaneHCID 123731,6-DiiodohexaneHCID 230286692-Chloro-3-(4-chlorophenylsulfonylmethyl)pyridineHCID 178418339Butyllithium

生成物 1

HCID 597507502-Chloro-3-[1-(4-chlorophenylsulfonyl)cycloheptyl]pyridine収率 32%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
-78 °C

実験手順

At −78° C., butyl lithium (a 1.57M hexane solution; 0.62 ml, 0.966 mmol) was added dropwise to a dimethoxyethane (5 ml) solution of the 2-chloro-3-(4-chlorophenylsulfonylmethyl)pyridine (146 mg, 0.483 mmol) obtained in Example 98. At −78° C., the resulting mixture was stirred for 20 minutes, followed by the addition of 1,6-diiodohexane (0.095 ml, 0.580 mmol). The temperature of the reaction mixture was gradually raised to room temperature, at which stirring was performed for 4 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 yield the title compound (60 mg, 32%) 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.

後処理

  1. customAt −78° C.
  2. temperatureThe temperature of the reaction mixture was gradually raised to room temperature, at which
  3. stirringstirring
  4. waitwas performed for 4 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 15% ethyl acetate/hexane eluate
  11. concentrationwas concentrated under reduced pressure
  12. customThe residue thus obtained
  13. customwas purified by high performance liquid chromatography (

出典と根拠

ORDレコード
ord-6ee14a74dfdf4ef09e627c0552402ba8
出典データセット
uspto-grants-2008_07
特許番号
US07399775B2

関連ノート

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