Chloroform → 2-(4-bromo-2-methoxyphenoxy)tetrahydro-2H-pyran

HRID 15062

Reaktionsgleichung

Reaktionsgleichung von HRID 15062
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(Cl)(Cl)Cl.[Br:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([O:36][CH3:37])[CH:30]=1>[Cl-].[Na+].O>[Br:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:6]2[CH2:5][CH2:4][CH2:3][CH2:2][O:1]2)=[C:31]([O:36][CH3:37])[CH:30]=1

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 80803,4-dihydro-2H-pyranHCID 2622344-Bromo-2-methoxyphenolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Produkt 1

HCID 684306542-(4-bromo-2-methoxyphenoxy)tetrahydro-2H-pyranAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

3,4-Dihydro-2H-pyran (2.0 mL) and pyridinium p-toluenesulfonate (370 mg) were added to chloroform solution (30 mL) of 4-bromo-2-methoxyphenol (3.0 g) and stirred at room temperature for 12 hours. Saturated brine was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with water and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:19) to provide the title compound (3.64 g, 86%).

Aufarbeitung

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentrating the solvent under reduced pressure
  5. customthe residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:19)

Quellen und Nachweise

ORD-Eintrag
ord-bbb5dbd2e2ab41958523662e95cd9384
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732456B2

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