Sodium hydride → Methyl 1-[3-(2-dioxolanyl)-propoxy]-pyrazole-4-carboxylate

HRID 232018

Reaktionsgleichung

Reaktionsgleichung von HRID 232018
[H-].[Na+].[OH:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[N:5]1.[H][H].Cl[CH2:16][CH2:17][CH2:18][CH:19]1[O:23][CH2:22][CH2:21][O:20]1>CN(C)C=O>[O:20]1[CH2:21][CH2:22][O:23][CH:19]1[CH2:18][CH2:17][CH2:16][O:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[N:5]1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 5520722-(3-Chloropropyl)-1,3-dioxolaneHCID 13823205methyl 1-hydroxy-1H-pyrazole-4-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 13823206Methyl 1-[3-(2-dioxolanyl)-propoxy]-pyrazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

21.8 g of sodium hydride (80 percent strength suspension in mineral oil) is introduced into 1.5 l of dry dimethylformamide, and 90 g of methyl 1-hydroxypyrazole-4-carboxylate are added a little at a time to the stirred mixture. When the evolution of hydrogen is complete, stirring is continued for 30 minutes, after which 95.5 g of 2-(3-chloropropyl)-1,3-dioxolane are added dropwise and the mixture is kept at 120° C. for 10 hours. Thereafter, the dimethylformamide is distilled off under reduced pressure, the residue is taken up in methyl tertbutyl ether, and the solution is washed with water, boiled and evaporated down to give 151 g of a slightly colored oil which crystallizes completely. M.p. 40°-42° C. NMR (CDCl3): 7.82 s [1]; 7.70 s [1]; 4.50 t [1]; 4.39 t [2]; 3.85-3.95 m [4]; 3.80 s [3]; 1.75-1.95 m [4].

Aufarbeitung

  1. additionare added a little at a time to the stirred mixture
  2. waitthe mixture is kept at 120° C. for 10 hours
  3. distillationThereafter, the dimethylformamide is distilled off under reduced pressure
  4. washthe solution is washed with water
  5. customevaporated down
  6. customto give 151 g of a slightly colored oil which
  7. customcrystallizes completely

Quellen und Nachweise

ORD-Eintrag
ord-791b2994b05649d7bd5312224ebe8c00
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04851410

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