Sodium borohydride → (6-o-Tolylpyridin-3-yl)methanol

HRID 493393Notes

Reaction equation

HRID 493393 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][N:8]=1.[BH4-].[Na+]>C(O)C>[C:1]1([CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]=[CH:9][C:10]([CH2:11][OH:12])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 247296626-(2-Methylphenyl)pyridine-3-carbaldehyde

Product 1

HCID 24729916(6-o-Tolylpyridin-3-yl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.070 g (5.43 mmol) of 6-o-tolylnicotinaldehyde in 19 mL of ethanol at 0-5° C., was added 287 mg(7.5 mmol, 1.4 eq.) of sodium borohydride. After 2 h, the reaction mixture was quenched with saturated sodium bicarbonate solution and, after 30 min, partitioned between dichloromethane and brine. The organic extract was dried over magnesium sulfate and concentrated to give the indicated product as a colorless oil, 1.08 g, 100% yield.

Workup

  1. customthe reaction mixture was quenched with saturated sodium bicarbonate solution and, after 30 min
  2. custompartitioned between dichloromethane and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-be46d817115f47078c09952a97e3d274
Source dataset
uspto-grants-2009_05
Patent number
US07534763B2

Reaction notes

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