Sodium borohydride → (6-Chloro-2-methylpyridin-3-yl)methanol

HRID 385945Notes

Reaction equation

HRID 385945 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([CH3:12])[N:5]=1>CO>[Cl:3][C:4]1[N:5]=[C:6]([CH3:12])[C:7]([CH2:8][OH:9])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 447548676-Chloro-2-methylpyridine-3-carbaldehyde

Product 1

HCID 59525984(6-Chloro-2-methylpyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.73 g, 19.28 mmol) was added to a solution of 6-chloro-2-methylnicotinaldehyde (1.5 g, 9.64 mmol) in methanol (38.6 mL) at room temperature. The mixture was stirred for 2 hours, then quenched with water and saturated aqueous sodium bicarbonate, and extracted three times with ethyl acetate. The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford the title compound.

Workup

  1. customquenched with water and saturated aqueous sodium bicarbonate
  2. extractionextracted three times with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-793b09812c5f4bde9dc40ab0690a36f3
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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