Sodium borohydride → {1-[4-(Methanesulfonyl)phenyl]-1H-pyrazol-4-yl}methanol

HRID 2060081Notes

Reaction equation

HRID 2060081 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([CH:16]=[O:17])[CH:13]=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[BH4-].[Na+]>CO>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH:15]=[C:14]([CH2:16][OH:17])[CH:13]=[N:12]2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59406388HCID 59406388, compound

Product 1

HCID 59406331{1-[4-(Methanesulfonyl)phenyl]-1H-pyrazol-4-yl}methanolYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-methanesulfonyl-phenyl)-1H-pyrazole-4-carbaldehyde (2.0 g, 8.0 mmol, 1.00 equiv) in methanol (10 mL) was added sodium borohydride (0.3 g, 8.0 mmol, 1.0 equiv) in one portion. After 30 min at rt, the reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The organic phase was dried (sodium sulfate) and concentrated affording [1-(4-methanesulfonyl-phenyl)-1H-pyrazol-4-yl]-methanol (1.8 g). LCMS: (MH)+=253.1 (0.91 min).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried (sodium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-318df07e32b647c68593a07de014e79a
Source dataset
uspto-grants-2012_10
Patent number
US08278337B2

Reaction notes

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