1H-1,2,4-Triazole → 1-(4-Chloro-phenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl)-1-penten-3-ol

HRID 1262476Notes

Reaction equation

HRID 1262476 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2([C:13]([CH3:16])([CH3:15])[CH3:14])C[O:11]2)=[CH:4][CH:3]=1.[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)([OH:11])[C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 537788492-(4-Chlorophenyl-ethenyl)-2-tert.-butyl-oxirane

Product 1

HCID 541396801-(4-Chloro-phenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl)-1-penten-3-olYield 80.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 17.75 g (0.075 mol) of 2-(4-chlorophenyl-ethenyl)-2-tert.-butyl-oxirane and 6.9 g (0.1 mol) of 1,2,4-triazole in 30 ml of ethanol was heated in a bomb tube at 150° C. for 20 hours. The reaction mixture was thereafter concentrated, and the crystalline residue was stirred with ether. The solid material was then filtered off under suction and was recrystallized from acetonitrile. 17.7 g (77% of theory) of 1-(4-chloro-phenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl)-1-penten-3-ol of melting point 139°-141° C. were obtained.

Workup

  1. concentrationThe reaction mixture was thereafter concentrated
  2. filtrationThe solid material was then filtered off under suction
  3. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-7f3130f48bb545fa9044a50515f22446
Source dataset
uspto-grants-1984_06
Patent number
US04452625

Reaction notes

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