Water → HCID 20066175, compound

HRID 329952Notes

Reaction equation

HRID 329952 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:12][O:11]2)=[CH:4][CH:3]=1.[NH:18]1[CH:22]=[N:21][CH:20]=[N:19]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:18]2[CH:22]=[N:21][CH:20]=[N:19]2)([OH:11])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 14798Sodium HydroxideHCID 14537613HCID 14537613, compound

Product 1

HCID 20066175HCID 20066175, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 89 g (0.352 mol) of 2-(4-chlorophenylethyl)-2-pentyl-oxirane, 26.5 g (0.384 mol) of 1,2,4-triazole, 3.5 g (0.0875 mol) of sodium hydroxide, 1.2 ml of water and a spatula tipful of α,α'-azoisobutyronitrile in 175 ml of N-methylpyrrolidone is heated at 120° C. for 4 hours. After this the mixture is cooled to room temperature and concentrated by stripping off the solvent under reduced pressure, the remaining residue is dissolved in ethyl acetate 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=1:1). In this manner 53.2 g (47.0% of theory) of 1-(4-chlorophenyl)-3-(1,2,4-triazol-1-yl-methyl)-3-octanol are obtained in the form of a yellow oil.

Workup

  1. concentrationconcentrated
  2. dissolutionthe remaining residue is dissolved in ethyl acetate
  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=1:1)

Sources & evidence

ORD record
ord-569a91f63a2646b08c2b53fcaf2b82ec
Source dataset
uspto-grants-1990_01
Patent number
US04894383

Reaction notes

Loading…