Sodium borohydride → 2-(4-Bromo-1H-pyrazol-1-yl)-2-methylpropan-1-ol

HRID 2175262Notes

Reaction equation

HRID 2175262 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([C:7]([CH3:14])([CH3:13])[C:8](OCC)=[O:9])[CH:6]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[N:4][N:5]([C:7]([CH3:14])([CH3:13])[CH2:8][OH:9])[CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59231678Ethyl 2-(4-bromo-1H-pyrazol-1-yl)-2-methylpropanoate

Product 1

HCID 586592212-(4-Bromo-1H-pyrazol-1-yl)-2-methylpropan-1-olYield 89.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(4-bromo-1H-pyrazol-1-yl)-2-methylpropanoate (0.8 g, 3.06 mmol) in MeOH (10 mL) was added sodium borohydride (0.348 g, 9.19 mmol). The reaction was stirred at room temperature for 3 h and quenched with saturated NH4Cl solution. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated. The resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes) to afford the title compound (0.6 g, 89% yield) as a white powder. LCMS, [M+H]+=219.0.

Workup

  1. customquenched with saturated NH4Cl solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-c2650c980889427189bfb3dcc03e1ddf
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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