Methanol → 3-Pyridineacetic acid, ethyl ester, 1-oxide

HRID 1844011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844011
ClC1C=CC=C(C(OO)=[O:9])C=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]=1.CO.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][C:14]1[CH:13]=[N+:12]([O-:9])[CH:17]=[CH:16][CH:15]=1)[CH3:23]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 70297m-Chloroperbenzoic acidHCID 96490Ethyl 3-pyridylacetateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 42103603-Pyridineacetic acid, ethyl ester, 1-oxideAusbeute 124,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel3×

Versuchsvorschrift

m-Chloro perbenzoic acid (6.2 g, 36.06 mmol) in CHCl3 (30 mL) was added drop wise to a solution of ethyl 2-(pyridin-3-yl)acetate (3.5 g, 21.21 mmol) in CHCl3 (30 mL) at room temperature under nitrogen atmosphere and the resulting reaction mass was stirred at room temperature for 5 hours. The reaction was monitored by TLC (10% methanol in chloroform). The reaction mass was basified using aqueous NaHCO3 solution to pH 7 and extracted using CHCl3. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford 4.8 g of the crude product. LCMS: 60.09%, m/z=182.0 (M+1)

Aufarbeitung

  1. customthe resulting reaction mass
  2. extractionextracted
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-687397d066c243679035f1b64c09f428
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946260B2

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