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

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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)=[C:7]([CH3:20])[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>[CH3:20][C:7]1[CH:6]=[C:5]([OH:4])[CH:19]=[CH:18][C:8]=1[CH2:9][O:10][CH2:11][CH2:12][N:13]1[CH:17]=[CH:16][N:15]=[N:14]1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

A solution of 7.30 g (26.7. mmol) 1-[2-(4-Allyloxy-2-methyl-benzyloxy)-ethyl]-1H-[1,2,3]-triazole in 100 ml dichloromethane was added to a solution of 13.02 g (83.4 mmol) 1,3-dimethylbarbituric acid an 959 mg (0.8 mmol) Pd(PPh3)4 in 30 ml dichloromethane and stirred overnight at 40° C. The mixture was extracted with 3× sat. NaHCO3-solution. The combined aqueous phases were extracted with dichloromethane. The combined organic extracts were dried over Na2SO4. Solvents were distilled off and the residue was purified by chromatography on silica gel (heptane/ethyl acetate 1/1 to 0/1) to yield 3.30 g (53%) 3-Methyl-4-(2-[1,2,3]triazol-1-yl-ethoxymethyl)-phenol as a yellow solid melting at 92-93° C.

Aufarbeitung

extractionThe mixture was extracted with 3× sat. NaHCO3-solution
extractionThe combined aqueous phases were extracted with dichloromethane
dry with materialThe combined organic extracts were dried over Na2SO4
distillationSolvents were distilled off
customthe residue was purified by chromatography on silica gel (heptane/ethyl acetate 1/1 to 0/1)

Quellen und Nachweise

ORD-Eintrag: ord-d3699187efa9492f8d7af6088717a3ee
Quelldatensatz: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07432291B2

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