Water → HCID 14537614, compound

HRID 329948Notes

Reaction equation

HRID 329948 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([C:13]([CH3:18])([CH3:17])[CH2:14][CH2:15][CH3:16])[CH2:12][O:11]2)=[CH:4][CH:3]=1.[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1.[OH-].[Na+].O>CN1CCCC1=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([CH2:12][N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)([OH:11])[C:13]([CH3:18])([CH3:17])[CH2:14][CH2:15][CH3:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 14798Sodium HydroxideHCID 14537612HCID 14537612, compound

Product 1

HCID 14537614HCID 14537614, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 20.5 g (0.077 mol) of 2-(4-chlorophenylethyl)-2-(1,1-dimethylbutyl)-oxirane, 5.3 g (0.077 mol) of 1,2,4-triazole, 1.0 g (0.025 mol) of sodium hydroxide, 1 ml of water and a spatula tipful of α,α'-azoisoutyronitrile in 50 ml of N-methylpyrrolidone is heated at 120° C. for 5 hours. After this, the solution is cooled to room temperature and concentrated by stripping off the solvent under reduced pressure, the remaining residue is dissolved in acetic acid and washed three times with water, the organic phase is dried over sodium sulphate and the solvent is removed under reduced pressure. The residue is purified by column chromatography (silica gel; dichloromethane:ethyl acetate=4:1). In this manner 16.0 g (61.9% of theory) of 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl-methyl)-3-heptanol are obtained in the form of a yellow oil.

Workup

  1. concentrationconcentrated
  2. dissolutionthe remaining residue is dissolved in acetic acid
  3. washwashed three times with water
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is purified by column chromatography (silica gel; dichloromethane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-e67fc64b762f46119fcff22d2381e9bb
Source dataset
uspto-grants-1990_01
Patent number
US04894383

Reaction notes

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