Dimethylbarbituric acid → 4-(2-[1,2,3]Triazol-1-yl-ethoxymethyl)-phenol

HRID 33489

Reaktionsgleichung

C([O:4][C:5]1[CH:19]=[CH:18][C:8]([CH2:9][O:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[N:14]2)=[CH:7][CH:6]=1)C=C.CN1C(=O)CC(=O)N(C)C1=O>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:13]1([CH2:12][CH2:11][O:10][CH2:9][C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:19][CH:18]=2)[CH:17]=[CH:16][N:15]=[N:14]1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

A solution of 500 mg (1.93 mmol) 1-[2-(4-allyloxy-benzyloxy)-ethyl]-1H-[1,2,3]-triazole in 10 ml dichloromethane was added to a solution of 904 mg (5.79 mmol) 1,3-dimethylbarbituric acid and 58 mg (0.05 mmol) Pd(PPh3)4 in 20 ml dichloromethane and stirred for 4.5 h at 40° C. The mixture was extracted with 3×20 ml sat. NaHCO3-solution and 8 ml water and the combined aqueous phases were reextracted with 2×10 ml dichloromethane. The organic extracts were combined and dried over MgSO4. Solvents were distilled off and the residue purified by chromatography on silica gel (ethyl acetate) to yield 248 mg (59%) of the title compound.

Aufarbeitung

extractionThe mixture was extracted with 3×20 ml sat. NaHCO3-solution and 8 ml water
dry with materialdried over MgSO4
distillationSolvents were distilled off
customthe residue purified by chromatography on silica gel (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-16c37bc72604453e908e00c60aa3887d
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07429605B2

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