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

HRID 2113886Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

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.

Workup

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)

Sources & evidence

ORD record: ord-d3699187efa9492f8d7af6088717a3ee
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432291B2

Reaction notes

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