2-(Dimethylamino)ethanol → ethyl 3-(2-(dimethylamino)ethoxy)-1-methyl-1H-pyrazole-5-carboxylate

HRID 577734

Reaktionsgleichung

Reaktionsgleichung von HRID 577734
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:4]([CH3:12])[N:3]=1.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][O:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:4]([CH3:12])[N:3]=1

Komponenten

6

Edukt 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178469374HCID 178469374, Verbindung

Produkt 1

HCID 86679667ethyl 3-(2-(dimethylamino)ethoxy)-1-methyl-1H-pyrazole-5-carboxylateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl 3-hydroxy-1-methyl-1H-pyrazole-5-carboxylate (10 g, 58.8 mmol), 2-(dimethylamino)ethanol (5.76 g, 64.7 mmol) and PPh3 (21.6 g, 82.3 mmol) in anhydrous THF (200 mL) was added dropwise DIAD (16.6 g, 82.3 mmol) at 0° C. After the addition, the reaction mixture was stirred at rt overnight. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (CH2Cl2/MeOH 30:1) to give the title compound (5.6 g, 40% yield) as a brown oil.

Aufarbeitung

  1. additionAfter the addition
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica gel (CH2Cl2/MeOH 30:1)

Quellen und Nachweise

ORD-Eintrag
ord-22e3d8578f564a8bac41a583719ae55e
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040547B2

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