Sodium hydride → 2-[3-(4-Fluorophenyl)-1,2,4-triazole-1-yl]-1-(2-fluoro-4-trifluoromethylphenyl)-1-(1,2,4-triazole-1-ylmethyl)-ethanol

HRID 1732150Notes

Reaction equation

HRID 1732150 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1([CH2:15][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH2:14][O:13]1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:32]=[CH:31][NH:30][N:29]=2)=[CH:24][CH:23]=1.[H-].[Na+]>C(O)(C)(C)C>[F:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[N:32]=[CH:31][N:30]([CH2:14][C:12]([C:3]3[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]=3[F:1])([CH2:15][N:16]3[CH:20]=[N:19][CH:18]=[N:17]3)[OH:13])[N:29]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 202266732-(2-Fluoro-4-trifluoromethylphenyl)-2-(1,2,4-triazol-1-ylmethyl)oxiraneHCID 178505560HCID 178505560, compound

Product 1

HCID 202267022-[3-(4-Fluorophenyl)-1,2,4-triazole-1-yl]-1-(2-fluoro-4-trifluoromethylphenyl)-1-(1,2,4-triazole-1-ylmethyl)-ethanol

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

2-(2-Fluoro-4-trifluoromethylphenyl)-2-(1,2,4-triazole-1-ylmethyl)oxirane (0.4 g.) and 3-(4-fluorophenyl)-1,2,4-triazole (0.3 g.) were added to a solution of sodium hydride (0.1 g. of a 50% dispersion in oil) in tert-butyl alcohol (10 ml.) and the mixture was heated at 80° for 16 hours. The reaction mixture was evaporated to dryness and the residual gum was partitioned between ethyl acetate and water. The organic layer was separated, dried and evaporated to dryness. The residual gum was chromatographed on a K60 silica column, eluting successively with chloroform/petroleum ether (b.p. 60°-80° C.) 60/40 v/v, 70/30 v/v and 80/20 v/v, to give 2-[3-(4-fluorophenyl)-1,2,4-triazole-1-yl]-1-(2-fluoro-4-trifluoromethylphenyl)-1-(1,2,4-triazole-1-ylmethyl)-ethanol, m.p. 96°-100°.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residual gum was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated to dryness
  6. customThe residual gum was chromatographed on a K60 silica column
  7. washeluting successively with chloroform/petroleum ether (b.p. 60°-80° C.) 60/40 v/v, 70/30 v/v and 80/20 v/v

Sources & evidence

ORD record
ord-af3805ec18a144dc908710814af63e8b
Source dataset
uspto-grants-1986_11
Patent number
US04625036

Reaction notes

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