1-(Phenylsulfonyl)-3-indolecarboxaldehyde → [1-(Phenylsulfonyl)-1H-Indol-3-Yl]Methanol

HRID 254188

Reaktionsgleichung

Reaktionsgleichung von HRID 254188
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH:19]=[O:20])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>ClCCl>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH2:19][OH:20])=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 3633341-(Phenylsulfonyl)-3-indolecarboxaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 2776213[1-(Phenylsulfonyl)-1H-Indol-3-Yl]Methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a three necked round bottom flask equipped with pressure equalizing funnel, 1-Benzenesulfonyl-1H-indole-3-carboxaldehyde (D1, 2.86 g, 0.01 mole) and dichloromethane (8 mL) were taken. Sodiumborohydride (0.005-0.01 mole) was added slowly at room temperature and the reaction mixture was stirred well for next 3-4 hours. After the completion of reaction (TLC, 3-5 hours), the product was isolated by distillation under reduced pressure. The residue was extracted with ethyl acetate (2×25 mL). The combined organic extracts were washed with water, followed by brine, dried over anhydrous sodium sulfate. The organic layer was evaporated under vacuum. The residue was generally an oily liquid, which was isolated and purified by flash chromatography (silica gel, EtOAc/Hexane, 2/8) to afford the title compound, which was identified by IR, NMR and mass spectral analyses.

Aufarbeitung

  1. customIn a three necked round bottom flask equipped with pressure
  2. customAfter the completion of reaction (TLC, 3-5 hours)
  3. customthe product was isolated by distillation under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate (2×25 mL)
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe organic layer was evaporated under vacuum
  8. customwhich was isolated
  9. custompurified by flash chromatography (silica gel, EtOAc/Hexane, 2/8)

Quellen und Nachweise

ORD-Eintrag
ord-9ca9b0b001ad42f6888f802779050f34
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875605B2

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