Sodium hydride → 4-(4-fluorophenyl)-1-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]butane-1,3-dione

HRID 2074117Notes

Reaction equation

HRID 2074117 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=[O:15])[CH3:14])[N:10]=[N:9]2)=[CH:5][CH:4]=1.[H-].[Na+].C[O:21][C:22](=O)[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1>C1COCC1>[F:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][C:22](=[O:21])[CH2:14][C:13]([C:11]2[N:10]=[N:9][N:8]([CH2:7][C:6]3[CH:16]=[CH:17][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:12]=2)=[O:15])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2733233Methyl 2-(4-fluorophenyl)acetateHCID 529111011-{1-[(4-methoxyphenyl)methyl]-1H-1,2,3-triazol-4-yl}ethan-1-one

Product 1

HCID 670922894-(4-fluorophenyl)-1-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]butane-1,3-dioneYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]ethanone (1.0 g, 4.30 mmol) in anhydrous THF (25 mL) was added NaH (0.38 g, 9.5 mmol) at 0° C. The mixture was stirred at RT for 1 hour, and (4-fluoro-phenyl)-acetic acid methyl ester (1.67 g, 10.0 mmol) was added at 0° C. and the mixture was refluxed overnight. The reaction mixture was evaporated and the residue was purified via column chromatography (silica gel, EtOAc/Petroleum ether 1:5) to yield the title compound (0.6 g, 38.0%) as a colorless oil.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified via column chromatography (silica gel, EtOAc/Petroleum ether 1:5)

Sources & evidence

ORD record
ord-f8c0a0c8f8624dbab9d971d6fc6c6733
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

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