Water → HCID 10946371, compound

HRID 1440379Notes

Reaction equation

HRID 1440379 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][C:7]2([C:10]3([F:13])[CH2:12][CH2:11]3)[CH2:9][O:8]2)=[CH:4][CH:3]=1.[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1.O>CN(C)C=O>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][C:7]([C:10]2([F:13])[CH2:12][CH2:11]2)([OH:8])[CH2:9][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 22400786HCID 22400786, compound

Product 1

HCID 10946371HCID 10946371, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3.3 g (15.7 mmol) of 2-(4-chlorobenzyl)-2-(1-fluorocyclopropyl)-oxirane in 10 ml of dimethylformamide is added dropwise to a mixture of 3.3 g (47.1 mmol) of 1,2,4-triazole and 0.35 g (3.14 mmol) of potassium tert.-butylate in 20 ml of dimethylformamide at a temperature of 80° C., while stirring. When the addition has ended, the reaction mixture is stirred for 13 hours at 80° C. The solvent is then stripped off under reduced pressure, and the remaining residue is taken up with water. The aqueous phase is extracted four times with methylene chloride. The combined organic phases are dried over sodium sulphate and then concentrated under reduced pressure. The remaining residue is chromatographed over silica gel using cyclohexane:ethylacetate=2:1 as the mobile phase. Evaporation of the eluate gives 2.2 g (47% of theory) of 1-(4-chlorophenyl)-2-(1-fluorocyclopropyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol in form of a solid substance. 1H-NMR (200 MHz, CDCl3): δ0.0-0.8 (m, 4H); 3.0 (AB-system, 2H); 4.01 (s,lH, OH); 4.3 (AB-system, 2H); 7.28 7.98 (s, 1H); 8, 13 (s, 1H).

Workup

  1. additionWhen the addition
  2. stirringthe reaction mixture is stirred for 13 hours at 80° C
  3. extractionThe aqueous phase is extracted four times with methylene chloride
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe remaining residue is chromatographed over silica gel
  7. customEvaporation of the eluate

Sources & evidence

ORD record
ord-b36b07673eb844b8b26c831b605cf3ea
Source dataset
uspto-grants-1996_03
Patent number
US05498750

Reaction notes

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