Sodium borohydride → HCID 67252978, compound

HRID 41598Notes

Reaction equation

HRID 41598 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([N:10]2[N:14]=[CH:13][CH:12]=[N:11]2)=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([N:10]2[N:14]=[CH:13][CH:12]=[N:11]2)=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866724452-methyl-5-(2H-1,2,3-triazol-2-yl)benzaldehyde

Product 1

HCID 67252978HCID 67252978, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-methyl-5-(2H-1,2,3-triazol-2-yl)benzaldehyde (140 mg, 0.75 mmol) in methanol (10 mL), NaBH4 (42 mg, 1.1 mmol) was added at 10° C. and stirred for 10 min. Then the mixture was allowed to warm to rt and stirred for 1 h. The mixture was quenched with saturated aqueous NH4Cl solution (0.3 mL) and filtered over hyflow. The filtrate was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified flash column chromatography (eluent: 30% ethyl acetate in hexane) to yield the title compound (100 mg, 71%). [TLC Rf=0.18 (ethyl acetate/hexane 30:70)].

Workup

  1. stirringstirred for 1 h
  2. customThe mixture was quenched with saturated aqueous NH4Cl solution (0.3 mL)
  3. filtrationfiltered over hyflow
  4. dry with materialThe filtrate was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified flash column chromatography (eluent: 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d8c95a0dbc484268999aa328ae7e3d70
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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