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

HRID 402430Notes

Reaction equation

HRID 402430 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-1e0d29d99b474aa2a2ddb130434e0034
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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