Sodium borohydride → 4-(2H-1,2,3-Triazol-2-yl)benzenemethanol

HRID 2216658Notes

Reaction equation

HRID 2216658 reaction equation
[N:1]1[N:2]([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=2)[N:3]=[CH:4][CH:5]=1.[BH4-].[Na+]>C1COCC1.CO>[N:1]1[N:2]([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][OH:11])=[CH:12][CH:13]=2)[N:3]=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 107973024-(2H-1,2,3-triazol-2-yl)benzaldehyde

Product 1

HCID 219436964-(2H-1,2,3-Triazol-2-yl)benzenemethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 42.26 g (244 mmol) of 4-[1,2,3]-triazol-2-yl-benzaldehyde in 140 ml of THF and 420 ml of MeOH, 9.23 g (244 mmol) of NaBH4 are added portionwise at 0–5° C. and the mixture is stirred for 30 min. at the same temperature. The reaction is quenched with sat. NH4Cl at 0–5° C. and the mixture is extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure to give the title compound as a colorless solid.

Workup

  1. customThe reaction is quenched with sat. NH4Cl at 0–5° C.
  2. extractionthe mixture is extracted with AcOEt
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-936aa10a07a04a97a4a814eeef6d73b9
Source dataset
uspto-grants-2006_09
Patent number
US07112611B2

Reaction notes

Loading…