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

HRID 2220254Notes

Reaction equation

HRID 2220254 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-f84e07ea282143728995f2f0f4a60e0a
Source dataset
uspto-grants-2008_08
Patent number
US07417028B2

Reaction notes

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