Triphenylphosphine → Methyl [3-[2-(1,6-dihydro-6-oxo-3,4-diphenyl-1-pyridazinyl)ethyl]phenoxyacetate]

HRID 981477

Reaktionsgleichung

N(C(OCC)=O)=NC(OCC)=O.[C:13]1([C:19]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:23][NH:22][C:21](=[O:31])[CH:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O[CH2:33][CH2:34][C:35]1[CH:36]=[C:37]([CH:44]=[CH:45][CH:46]=1)[O:38][CH2:39][C:40]([O:42][CH3:43])=[O:41].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[O:31]=[C:21]1[N:22]([CH2:33][CH2:34][C:35]2[CH:36]=[C:37]([CH:44]=[CH:45][CH:46]=2)[O:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])[N:23]=[C:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:20]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Diethyl azodicarboxylate (2.73 g, 2.50 mL, 16 mmol) was added to a stirred solution of 5,6-diphenyl-3(2H)-pyridazinone (3.00 g, 12 mmol), methyl [3-(2-hydroxyethyl)-phenoxy]acetate (2.80 g, 13 mmol) and triphenylphosphine (4.12 g, 16 mmol) in dry THF (75 mL) maintained at 0° C. The ice bath was removed and the mixture stirred at room temperature for 1.75 hours before removal of the solvent. The residue was chromatographed twice on columns of silica gel using mixtures of diethyl ether and hexanes (7:3) and then (3:2) as eluent to give methyl [3-[2-(1,6-dihydro-6-oxo-3,4-diphenyl-1-pyridazinyl)ethyl]phenoxyacetate] (5.12 g, 98%), contaminated with 0.6 equivalents of 1,2-dicarbethoxy hydrazine, as a white foam.

Aufarbeitung

customThe ice bath was removed
customThe residue was chromatographed twice on columns of silica gel using mixtures of diethyl ether and hexanes (7:3)

Quellen und Nachweise

ORD-Eintrag: ord-13373c8e04cb4fada8a204b37e54929c
Quelldatensatz: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04992439

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