Dimethylformamide → (2R,3R)-1,3-bis(1H-1,2,4-triazol-1-yl)-2-(2-fluorophenyl)-2-butanol

HRID 2397007Notes

Reaction equation

HRID 2397007 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C@@:13]1([CH2:17][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[C@H:15]([CH3:16])[O:14]1.C(=O)([O-])[O-].[Li+].[Li+].CN(C)C=O>C(OCC)(=O)C>[N:18]1([CH2:17][C@@:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[F:6])([OH:14])[C@H:15]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[CH3:16])[CH:22]=[N:21][CH:20]=[N:19]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 92571H-1,2,4-TriazoleHCID 11125Lithium CarbonateHCID 104439761-(((2R,3S)-2-(2-fluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole

Product 1

HCID 54470397(2R,3R)-1,3-bis(1H-1,2,4-triazol-1-yl)-2-(2-fluorophenyl)-2-butanolYield 50.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1H-1,2,4-triazole (1.17 g), (2R,3S)-2-(2-fluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane (2 g), lithium carbonate (6.32 g) and dimethylformamide (40 ml) was stirred for 24 hours at 110° C. After cooling, to the mixture was added ethyl acetate (50 ml). The mixture was filtered to remove insoluble substances. The filtrate was distilled under reduced pressure. The residue was dissolved in ethyl acetate (100 ml). The mixture was washed with saturated saline (30 ml×2). The ethyl acetate layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure. The residue was purified by silica gel chromatography (silica gel 50 g, eluent: ethyl acetate/acetone=4:1) to give (2R,3R)-1,3-bis(1H-1,2,4-triazol-1-yl)-2-(2-fluorophenyl)-2-butanol (1.32 g).

Workup

  1. temperatureAfter cooling, to the mixture
  2. filtrationThe mixture was filtered
  3. customto remove insoluble substances
  4. distillationThe filtrate was distilled under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  6. washThe mixture was washed with saturated saline (30 ml×2)
  7. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  8. distillationdistilled under reduced pressure
  9. customThe residue was purified by silica gel chromatography (silica gel 50 g, eluent: ethyl acetate/acetone=4:1)

Sources & evidence

ORD record
ord-404c1a4423ab4d8ebc46e96901d9d32a
Source dataset
uspto-grants-1996_02
Patent number
US05495024

Reaction notes

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