Benzenesulfonyl chloride → 1-(Phenylsulfonyl)-1,5,6,7-tetrahydro-4H-indol-4-one

HRID 2086937

反応式

HRID 2086937 の反応式
[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[O:10])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[C:13]1([S:19]([N:1]2[C:9]3[CH2:8][CH2:7][CH2:6][C:5](=[O:10])[C:4]=3[CH:3]=[CH:2]2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 2802291,5,6,7-Tetrahydro-4H-indol-4-one

生成物 1

HCID 134377091-(Phenylsulfonyl)-1,5,6,7-tetrahydro-4H-indol-4-one収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A stirred solution of 1,5,6,7-tetrahydro-4H-indol-4-one (5.0 g, 37.0 mmol) in THF is treated portionwise with NaH (60% dispersion in mineral oil, 1.5 g, 37.0 mmol) under N2 at room temperature, stirred for 0.5 hr, treated with benzene sulfonyl chloride (4.7 ml, 37.0 mmol), stirred for 24 hr, quenched with water and diluted with EtOAc. The phases are separated. The organic phase is washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, EtOAc/hexanes, 1/1 as eluent) to afford the title product as an off-white solid, 8.72 g (85% yield), mp 108-110° C., identified by NMR and mass spectral analyses.

後処理

  1. stirringstirred for 24 hr
  2. customquenched with water
  3. additiondiluted with EtOAc
  4. customThe phases are separated
  5. washThe organic phase is washed sequentially with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is purified by flash chromatography (silica gel, EtOAc/hexanes, 1/1 as eluent)

出典と根拠

ORDレコード
ord-8094538fe8ee497da0857f8a1ee97d97
出典データセット
uspto-grants-2004_04
特許番号
US06727270B2

関連ノート

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