Benzylsulfonic acid → 5-(Phenylmethoxy)-1-phenylsulfonylindole

HRID 1159826

Reaktionsgleichung

Reaktionsgleichung von HRID 1159826
C(C1C=CC2C(=CC(=O)N=2)C=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18](S(O)(=O)=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[S:29]([O-:33])([O-])(=O)=[O:30].C([N+:38]([CH2:47][CH2:48][CH2:49][CH3:50])([CH2:43][CH2:44][CH2:45][CH3:46])CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-:68].[Na+]>C(Cl)Cl>[CH2:18]([O:68][C:46]1[CH:50]=[C:49]2[C:43](=[CH:44][CH:45]=1)[N:38]([S:29]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:33])=[O:30])[CH:47]=[CH:48]2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 7532Benzylsulfonic acidHCID 14798Sodium HydroxideHCID 11433187Bis(tetrabutylammonium) sulphateHCID 687142165-Benzyloxoindole

Produkt 1

HCID 118246245-(Phenylmethoxy)-1-phenylsulfonylindoleAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

DCM (200 mL) was added to 5-benzyloxoindole (15 g, 67 mmol), benzylsulfonic acid (17.8 g, 101 mmol) and tetrabutyl ammoniumsulfat (6.84 g, 20 mmol) followed by 5 M NaOH (40 mL). The reaction mixture was stirred at rt for 3 h. The aqueous layer was washed with DCM (2×30 mL) and the organic layers were combined and washed with brine (30 mL). Drying (MgSO4) and concentration in vacco was followed by crystallization from MeOH to give the product in 83% yield (20.3 g).

Aufarbeitung

  1. washThe aqueous layer was washed with DCM (2×30 mL)
  2. washwashed with brine (30 mL)
  3. customDrying
  4. concentration(MgSO4) and concentration in vacco
  5. customwas followed by crystallization from MeOH
  6. customto give the product in 83% yield (20.3 g)

Quellen und Nachweise

ORD-Eintrag
ord-d000031967a94d8a974ac43d6a24285f
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812017B2

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