Water → HCID 53708840, compound

HRID 1253273Notes

Reaction equation

HRID 1253273 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2(O)[C:19]([CH3:21])([CH3:20])[CH2:18][CH2:17][O:16]2)[N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[C:15]2[C:19]([CH3:21])([CH3:20])[CH2:18][CH2:17][O:16]2)[N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 13561746HCID 13561746, compound

Product 1

HCID 53708840HCID 53708840, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5 g (0.0155 mole) of 1-(4-chlorophenyl)-2-(3,3-dimethyl-2-hydroxy-tetrahydrofuran-2-yl)-2-(1,2,4-triazol-1-yl)-ethane are dissolved in 100 ml of toluene, 0.5 g of p-toluenesulphonic acid are added and the mixture is heated under reflux for 2 hours, using a water separator. The reaction mixture is cooled, washed with water, dried over sodium sulphate and concentrated in vacuo. The residue is purified by column chromatography (silica gel; ethyl acetate/cyclohexane=3:1). 2.8 g (59.6% of theory) of 1-(4-chlorophenyl-2-(3,3-dimethyl-tetrahydrofuran-2-ylidene)-2-(1,2,4-triazol-1-yl)-ethane are obtained as form A of melting point 89° C. and 0.4 g (8.5% of theory) of 1-(4-chlorophenyl)-2-(3,3-dimethyl-tetrahydrofuran-2-ylidene)-2-(1,2,4-triazol-1-yl)-ethane are obtained as form B of melting point 175°-177° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction mixture is cooled
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by column chromatography (silica gel; ethyl acetate/cyclohexane=3:1)

Sources & evidence

ORD record
ord-58bb26db68974e4f989baaf3b29ec27e
Source dataset
uspto-grants-1988_05
Patent number
US04748249

Reaction notes

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