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4-Toluenesulfonyl chloride → 3-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]phenyl}sulfanyl)propyl 4-methylbenzenesulfonate

HRID 70593
ノート
印刷プレビュー

反応式

HRID 70593 の反応式
C(N(CC)CC)C.Cl.CN(C)C.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.[Cl:24][C:25]1[CH:30]=[C:29](/[C:31](/[C:38]2[CH:43]=[CH:42][C:41]([CH2:44][CH3:45])=[C:40]([O:46][CH3:47])[N:39]=2)=[CH:32]\[CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[CH:28]=[CH:27][C:26]=1[S:48][CH2:49][CH2:50][CH2:51][OH:52]>C(Cl)(Cl)Cl.O>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:52][CH2:51][CH2:50][CH2:49][S:48][C:26]2[CH:27]=[CH:28][C:29](/[C:31](/[C:38]3[CH:43]=[CH:42][C:41]([CH2:44][CH3:45])=[C:40]([O:46][CH3:47])[N:39]=3)=[CH:32]\[CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:30][C:25]=2[Cl:24])(=[O:22])=[O:21])=[CH:16][CH:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10313079Trimethylamine HydrochlorideHCID 673999143-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]phenyl}sulfanyl)propan-1-ol

生成物 1

HCID 866580103-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]phenyl}sulfanyl)propyl 4-methylbenzenesulfonate
収率 93.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

Triethylamine (87 μL), trimethylamine hydrochloride (20 mg) and 4-methylbenzenesulfonyl chloride (60 mg) were sequentially added to a solution of 3-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]phenyl}sulfanyl)propan-1-ol (95 mg) in chloroform (2 mL) under ice-cooling, and the mixture was stirred at room temperature for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure to give 3-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]phenyl}sulfanyl)propyl 4-methylbenzenesulfonate (120 mg) as a yellow amorphous.

後処理

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customafter which the solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-742d30bd0979473baa9dfa3816a23980
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822503B2

反応ノート

読み込み中…

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