1-(4-Chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one → 1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-ol

HRID 1447022Notes

Reaction equation

HRID 1447022 reaction equation
[N:1]1([CH2:6][C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[O:8])[CH:5]=[N:4][CH:3]=[N:2]1.[BH4-].[Na+]>CO>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH:7]([OH:8])[CH2:6][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 7164721-(4-Chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 5580621-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of α-1,2,4-triazol-1-yl-p-chloroacetophenone (4 g) in methanol (12 ml) was treated with sodium borohydride (0.5 g) with cooling and stirring. The mixture was then left at room temperature for 0.5 hour and refluxed for 1 hour. The methanol was removed under reduced pressure and water (25 ml) was added followed by dilute hydrochloric acid (10 ml). The white solid was filtered, washed with water and dried. Crystallisation from ethyl acetate-petroleum ether (60°-80°) gave the title compound as a white crystalline solid.

Workup

  1. temperaturewith cooling
  2. temperaturerefluxed for 1 hour
  3. customThe methanol was removed under reduced pressure and water (25 ml)
  4. additionwas added
  5. filtrationThe white solid was filtered
  6. washwashed with water
  7. customdried
  8. customCrystallisation from ethyl acetate-petroleum ether (60°-80°)

Sources & evidence

ORD record
ord-44616e3a8eeb416784bc4b10514c1f44
Source dataset
uspto-grants-1982_02
Patent number
US04315016

Reaction notes

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