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

HRID 2086937

Reaktionsgleichung

Reaktionsgleichung von HRID 2086937
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-8094538fe8ee497da0857f8a1ee97d97
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727270B2

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