Ethyl diazoacetate → Diethyl 4-[(4-chloro-2-nitrophenyl)hydroxymethyl]-1H-pyrazole-3,5-dicarboxylate

HRID 1954727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1954727
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:16])[C:9]#[C:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1.[N+:20](=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N-:21]>C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:16])[C:9]2[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:20][NH:21][C:10]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1

Komponenten

4

Edukt 2

HCID 12192Ethyl diazoacetateHCID 18358875Ethyl 4-(4-chloro-2-nitrophenyl)-4-hydroxy-2-butynoate

Produkt 1

HCID 18358881Diethyl 4-[(4-chloro-2-nitrophenyl)hydroxymethyl]-1H-pyrazole-3,5-dicarboxylateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of ethyl 4-(4-chloro-2-nitrophenyl)-4-hydroxy-2-butynoate (5.00 g, 17.7 mmol) and ethyl diazoacetate (2.75 g, 26.5 mmol) in diethyl ether (43.3 mL) was refluxed for 5 days. After cooling to room temperature the reaction mixture was chromatographed eluting with ethyl acetate:hexanes (20:80, 30:70, 40:60, and 50:50). All of the fractions containing the desired compound were combined, concentrated on the rotary evaporator, and the product was recrystallized twice from toluene (total volume 225 mL) to give the title compound as a white solid (4.15 g, 59%, mp 60° C.).

Aufarbeitung

  1. customwas chromatographed
  2. washeluting with ethyl acetate:hexanes (20:80, 30:70, 40:60, and 50:50)
  3. additionAll of the fractions containing the desired compound
  4. concentrationconcentrated on the rotary evaporator
  5. customthe product was recrystallized twice from toluene (total volume 225 mL)

Quellen und Nachweise

ORD-Eintrag
ord-962836f9a1d24b5ea8c23621aec85e73
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06124281

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