Methanol → Methyl 3-(1H-Imidazol-5-Yl)Propanoate

HRID 870606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870606
S(Cl)(Cl)=O.[NH:5]1[C:9]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:8][N:7]=[CH:6]1.[CH3:15]O>>[NH:5]1[C:9]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][N:7]=[CH:6]1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 706301H-Imidazole-5-propanoic acid

Produkt 1

HCID 565491Methyl 3-(1H-Imidazol-5-Yl)PropanoateAusbeute 100 %

Versuchsvorschrift

Add thionyl chloride (0.75 mL) to a −78° C. solution of 3-(1H-imidazol-5-yl)propanoic acid (2.0 g; 1.0 equiv; 14.27 mmoles) in methanol (18 mL). Allow the reaction mixture to warm to ambient temperature and stir for 30 minutes. Add saturated sodium bicarbonate (10 mL) to the reaction mixture and concentrate. Suspended the resulting residue in methanol (10 mL) and filter, then concentrate to afford methyl 3-(1H-imidazol-5-yl)propanoate (2.2 g; 100%) as a white solid: MS (m/z): 155(M+1).

Aufarbeitung

  1. concentrationAdd saturated sodium bicarbonate (10 mL) to the reaction mixture and concentrate
  2. filtrationfilter
  3. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-ccf8d6c040c248cea7fba67c38a2a160
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969555B2

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