Methanol → (6-(Benzyloxy)pyridin-3-yl)methanol

HRID 78201Notes

Reaction equation

HRID 78201 reaction equation
CO.[CH2:3]([O:10][C:11]1[N:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[BH4-].[Na+]>O>[CH2:3]([O:10][C:11]1[N:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 211022056-(Benzyloxy)nicotinaldehyde

Product 1

HCID 59255139(6-(Benzyloxy)pyridin-3-yl)methanolYield 91.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a methanol (20.0 mL) solution of 6-benzyloxy-pyridine-3-carbaldehyde (2.00 g, 9.38 mmol) described in Manufacturing Example 12-1-2 was added sodium borohydride (426 mg, 11.3 mmol) on an ice bath (0° C.) under nitrogen atmosphere, which was stirred for 10 minutes at room temperature. Water was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure to obtain the title compound (1.84 g, 91.1%).

Workup

  1. extractionwhich was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-c2e05d31d6114430b843ce63f362ebe6
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

Loading…