Sodium borohydride → (1-ethyl-1H-pyrazol-5-yl)Methanol

HRID 577130Notes

Reaction equation

HRID 577130 reaction equation
[BH4-].[Na+].[CH2:3]([N:5]1[C:9]([CH:10]=[O:11])=[CH:8][CH:7]=[N:6]1)[CH3:4]>CO>[CH2:3]([N:5]1[C:9]([CH2:10][OH:11])=[CH:8][CH:7]=[N:6]1)[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 70095341-ethyl-1H-pyrazole-5-carbaldehyde

Product 1

HCID 23006116(1-ethyl-1H-pyrazol-5-yl)Methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of sodium borohydride (686 mg, 18.1 mmol) in methanol (40 mL) was added a solution of 1-ethyl-1H-pyrazole-5-carbaldehyde (1.5 g, 12.1 mmol) in methanol (10 mL) at 0° C. The mixture was stirred for 2.5 hours at room temperature. The solvent was evaporated, water was added, and the mixture was extracted 3 times with ethyl acetate. The combined organic phases were washed with brine and dried over sodium sulfate. After evaporation of solvent, (1-ethyl-1H-pyrazol-5-yl)methanol was obtained as a colorless oil (1.07 g, 70% yield) and used in the next step without further purification; 1H NMR (400 MHz, DMSO-d6): δ 1.31 (t, J=7.2 Hz, 3H), 4.10 (q, J=7.2 Hz, 2H), 4.49 (d, J=5.5 Hz, 2H), 5.25 (t, J=5.5 Hz, 1H), 6.12 (d, J=1.5 Hz, 1H), 7.31 (d, J=1.5 Hz, 1H).

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. extractionthe mixture was extracted 3 times with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customAfter evaporation of solvent

Sources & evidence

ORD record
ord-fd875bd0114340d5bd71d6f169821042
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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