Phosphorus oxychloride → 3-(chloromethyl)-1-tosyl-1H-indole

HRID 41535

Reaktionsgleichung

Reaktionsgleichung von HRID 41535
[S:1]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20]O)=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].O=P(Cl)(Cl)[Cl:24]>C1COCC1>[Cl:24][CH2:20][C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]([S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])[CH:12]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 839263(1-tosyl-1H-indol-3-yl)methanol

Produkt 1

HCID 668519953-(chloromethyl)-1-tosyl-1H-indoleAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (1-tosyl-1H-indol-3-yl)methanol (1.0 g, 3.318 mmol) in dry THF (10 mL), POCl3 (0.661 g, 4.314 mmol) was added at 0° C. and the mixture was stirred for 10 min. The reaction mixture was allowed to warm to ambient temperature and refluxed for 3 h. The solvent was removed under reduced pressure at 45° C. and the crude reaction mixture was quenched with saturated NaHCO3 solution and extracted with DCM. The organic layer was separated and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield the title compound as a solid (1.04 g, 98%).

Aufarbeitung

  1. temperaturerefluxed for 3 h
  2. customThe solvent was removed under reduced pressure at 45° C.
  3. customthe crude reaction mixture
  4. customwas quenched with saturated NaHCO3 solution
  5. extractionextracted with DCM
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e45db4d755b9499d802a03d699de345d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530648B2

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