Methanol → 4-(Hydroxymethyl)pyridin-2(1H)-one

HRID 1475233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1475233
[O:1]=[C:2]1[CH:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[CH:4][NH:3]1.[H-].C([Al+]CC(C)C)C(C)C.CO.O>C1COCC1>[OH:9][CH2:8][C:6]1[CH:5]=[CH:4][NH:3][C:2](=[O:1])[CH:7]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 280755Methyl 2-oxo-1,2-dihydropyridine-4-carboxylateHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 110946104-(Hydroxymethyl)pyridin-2(1H)-oneAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 2-oxo-1,2-dihydropyridine-4-carboxylate (300 mg, 1.96 mmol) in THF (20 mL) was added diisobutylaluminium hydride (1.0 M in THF, 20 mL, 20 mmol). The mixture was stirred at RT for 3 h, then MeOH (2 mL) and H2O (1 mL) were added. The mixture was stirred at RT for 20 minutes and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (DCM:MeOH=8:1) to afford 4-(hydroxymethyl)pyridin-2(1H)-one as a white solid (150 mg, 61.2%). MS (ES+) C6H7NO2 requires: 125. found: 126 [M+H]+.

Aufarbeitung

  1. stirringThe mixture was stirred at RT for 20 minutes
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by silica gel chromatography (DCM:MeOH=8:1)

Quellen und Nachweise

ORD-Eintrag
ord-b06f4a02a1114cfdb2ed6cb8ab94b19a
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018380B2

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