Hydrochloric Acid → 1-[5-(1-Methylethoxy)pyridin-2-yl]ethanol

HRID 1038542

Reaktionsgleichung

Reaktionsgleichung von HRID 1038542
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[O:12])=[N:9][CH:10]=1)[CH3:3].[CH3:13][Mg]Br.Cl>O1CCCC1>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([OH:12])[CH3:13])=[N:9][CH:10]=1)[CH3:1]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 797940465-IsopropoxypicolinaldehydeHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 665985281-[5-(1-Methylethoxy)pyridin-2-yl]ethanolAusbeute 102,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5-(1-Methylethoxy)picolinaldehyde (24 mg, 0.145 mmol) was dissolved in tetrahydrofuran (1.5 mL), added methylmagnesium bromide (230 μL, 0.218 mmol) under ice-cold conditions, and the mixture was stirred at 0° C. for 0.5 hours. The mixture was further stirred at room temperature for 0.5 hours. The reaction solution was added 1N aqueous solution of hydrochloric acid and an aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and 1-[5-(1-methylethoxy)pyridin-2-yl]ethanol (27 mg (yield 98%)) was obtained as a brown oil.

Aufarbeitung

  1. stirringThe mixture was further stirred at room temperature for 0.5 hours
  2. extractionan aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1dadb22347164d7591c719642af44734
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551985B2

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