phosphorous acid, trisodium salt → 5-Cyclopropoxy-2-methylpyridine

HRID 1038578

Reaktionsgleichung

Reaktionsgleichung von HRID 1038578
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2(S(C3C=CC=CC=3)(=O)=O)[CH2:11][CH2:10]2)=[CH:4][N:3]=1.P([O-])([O-])[O-].[Na+].[Na+].[Na+].C(=O)([O-])O.[Na+]>CO.[Na].[Hg]>[CH:9]1([O:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[N:3][CH:4]=2)[CH2:11][CH2:10]1

Komponenten

6

Edukt 3

HCID 134681phosphorous acid, trisodium saltHCID 516892Sodium BicarbonateHCID 665983222-Methyl-5-[1-(phenylsulfonyl)cyclopropoxy]pyridine

Produkt 1

HCID 585206415-Cyclopropoxy-2-methylpyridineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9837419Sodium amalgamKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

2-Methyl-5-[1-(phenylsulfonyl)cyclopropoxy]pyridine (540 mg, 1.87 mmol) was dissolved in methanol (5.5 mL), added sodium phosphite (671 mg, 5.598 mmol), and sodium amalgam (3.58 g, 7.47 mmol) under ice-cold conditions, stirred at the same temperature for 30 minutes, and then stirred at room temperature for 3 hours. The reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate, and extracted with diethylether. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by distillation, and the title compound (240 mg (yield 86%)) was obtained as a yellow oil.

Aufarbeitung

  1. stirringstirred at room temperature for 3 hours
  2. extractionextracted with diethylether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. distillationThe obtained residue was purified by distillation

Quellen und Nachweise

ORD-Eintrag
ord-2043f59255d14c608041cd6193b3fe29
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551985B2

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