Triphenylphosphine → Dimethyl 4-nitro-1-(2-propoxyethyl)-1H-pyrazole-3,5-dicarboxylate
Reaktionsgleichung
[N+:1]([C:4]1[C:5]([C:13]([O:15][CH3:16])=[O:14])=[N:6][NH:7][C:8]=1[C:9]([O:11][CH3:12])=[O:10])([O-:3])=[O:2].[CH2:17]([O:20][CH2:21][CH2:22]O)[CH2:18][CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[N+:1]([C:4]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[N:7][N:6]([CH2:22][CH2:21][O:20][CH2:17][CH2:18][CH3:19])[C:5]=1[C:13]([O:15][CH3:16])=[O:14])([O-:3])=[O:2]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Dimethyl 4-nitro-1H-pyrazole-3,5-dicarboxylate (WO00/24745, page 48, preparation 2) (15 g, 60 mmol), 2-propoxyethanol (8.2 mL, 70 mmol) and triphenylphosphine (18.9 g, 70 mmol) were dissolved in tetrahydrofuran (150 mL) and the solution cooled to 0° C. The solution was treated with diisopropyl azodicarboxylate (14.2 mL, 70 mmol) and the reaction mixture stirred at 0° C. for 3 hours before being allowed to warm to room temperature. The reaction mixture was concentrated in vacuo and the residue purified by column chromatography on silica gel eluting with ethyl acetate:pentane 15:85 and then again eluting with dichloromethane to yield the title product. 1H NMR (CD3OD, 400 MHz) δ: 0.82 (t, 3H), 1.47 (q, 2H), 3.34 (t, 2H), 3.78 (t, 2H), 3.91 (s, 6H), 4.76 (t, 2H). MS APCI+ m/Z 316 [MH]+
Aufarbeitung
- temperatureto warm to room temperature
- concentrationThe reaction mixture was concentrated in vacuo
- customthe residue purified by column chromatography on silica gel eluting with ethyl acetate:pentane 15:85
- washagain eluting with dichloromethane
Quellen und Nachweise
- ORD-Eintrag
- ord-ad989db27d814a2096ff9be80acd0c16
- Quelldatensatz
- uspto-grants-2012_01
- Patentnummer
- US08097621B2
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