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

HRID 402365Notes

Reaction equation

HRID 402365 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]([CH3:15])[C:12]=1[CH:13]=[O:14].[BH4-].[Na+].[Cl-].[NH4+]>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]([CH3:15])[C:12]=1[CH2:13][OH:14]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 866647624-(2-Fluorophenyl)-1-methyl-1H-1,2,3-triazole-5-carbaldehyde

Product 1

HCID 67498210(4-(2-Fluorophenyl)-1-methyl-1H-1,2,3-triazol-5-yl)methanolYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(2-fluorophenyl)-1-methyl-1H-1,2,3-triazole-5-carbaldehyde (411 mg, 2.0 mmol) in MeOH (42 mL) was added sodiumborohydride (38 mg, 1.00 mmol) under Argon at room temperature and the reaction mixture was allowed to warm up to room temperature over 0.5 h. 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. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (360 mg, 87%) as a white solid. MS: m/e=208.1 [M+H]+.

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
  6. customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-2ef7107854bd4bacb7c315e16d79adee
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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