Formaldehyde → methyl 1-(hydroxymethyl)-1H-pyrazole-4-carboxylate

HRID 1983025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1983025
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][NH:8][CH:9]=1)=[O:4].[CH2:10]=[O:11].C(N(CC)CC)C>CC(C)=O>[OH:11][CH2:10][N:7]1[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:9]=[N:8]1

Komponenten

5

Edukt 3

HCID 712Formaldehyde2×HCID 8471Triethylamine2×HCID 9793760Methyl 1H-pyrazole-4-carboxylate

Produkt 1

HCID 23149172methyl 1-(hydroxymethyl)-1H-pyrazole-4-carboxylateAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

The mixture of 1.40 g of 4-methoxycarbonyl-1H-pyrazole, 0.37 g of paraformaldehyde and 0.11 g of triethylamine was stirred at 130° C. for 1 hour. 0.74 g of paraformaldehyde and 2 ml of triethylamine were added to the mixture and stirred at 130° C. for 2 hours. After the reaction mixture was cooled to room temperature, acetone was added. After the mixture was filtered, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.38 g of 1-(hydroxymethyl)-4-methoxycarbonyl-1H-pyrazole.

Aufarbeitung

  1. stirringstirred at 130° C. for 2 hours
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. filtrationAfter the mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-33722893bd724639b992c6a8f08dda9d
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07541374B2

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