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

HRID 1165706Notes

Reaction equation

HRID 1165706 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-chlorophenyl)-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-01d1507db344440e9b723e7c21ec836d
Source dataset
uspto-grants-1990_03
Patent number
US04911750

Reaction notes

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