Benzenesulfonyl chloride → Ethyl 2-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate

HRID 554273ノート

反応式

HRID 554273 の反応式
[Cl:1][C:2]1[NH:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[H-].[Na+].C1OCCOCCOCCOCCOC1.[C:35]1([S:41](Cl)(=[O:43])=[O:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O1CCCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[N:3]([S:41]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)(=[O:43])=[O:42])[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

参加物

7

反応物 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 14937509HCID 14937509、化合物

生成物 1

HCID 66924662Ethyl 2-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate収率 81.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution (40 mL) of ethyl 2-chloro-5-phenyl-1H-pyrrole-3-carboxylate (1.0 g) in tetrahydrofuran was added sodium hydride (60% in oil, 488 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (2.65 g) was added dropwise and the mixture was stirred for 30 min. Benzenesulfonyl chloride (1.84 g) was added, and the mixture was further stirred for 24 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=85:15), and crystallized from diisopropyl ether to give the title compound as colorless crystals (yield 1.27 g, 81%).

後処理

  1. stirringthe mixture was stirred for 30 min
  2. stirringthe mixture was further stirred for 24 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=85:15)
  8. customcrystallized from diisopropyl ether

出典と根拠

ORDレコード
ord-525a2afe98694402b3a7a629f5e738c6
出典データセット
uspto-grants-2011_11
特許番号
US08048909B2

反応ノート

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