Ammonium Chloride → (1-(4-Fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)methanol

HRID 2365221Notes

Reaction equation

HRID 2365221 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]=[O:14])=[C:11]([CH3:15])[N:10]=[N:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH2:13][OH:14])=[C:11]([CH3:15])[N:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 199146531-(4-Fluorophenyl)-4-methyl-1H-1,2,3-triazole-5-carbaldehyde

Product 1

HCID 19914681(1-(4-Fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)methanolYield 89.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazole-4-carbaldehyde (2.28 g, 11 mmol) in MeOH (180 mL) was added sodiumborohydride (210 mg, 6.0 mmol) at 0° C., and the resulting mixture stirred at 0° C. for 30 min, The mixture was then poured into saturated ammonium chloride solution and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated to afford the title compound (2.05 g, 89%) as a white solid. MS: m/e=208.2 [M]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe combined organic extracts washed with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-60a8ae4a0f6046c4b684673e1c534c16
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

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