Sodium borohydride → (6-Methoxypyridin-2-yl)methanol

HRID 911429Notes

Reaction equation

HRID 911429 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH:9]=[O:10])[CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>C1COCC1>[OH:10][CH2:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 123253926-Methoxy-2-pyridinecarboxaldehyde

Product 1

HCID 12325389(6-Methoxypyridin-2-yl)methanolYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-methoxy-pyridine-2-carbaldehyde (J. Org. Chem. 1990, 55, 69-73) (11.0 g, 80.3 mmol) in wet THF (200 mL) add portion wise with stirring sodium borohydride (3.0 g, 79 mmol) and continue stirring for 1 h at ambient temperature. Add brine, extract the reaction mixture twice with EtOAc, dry the organic layer over anhydrous Na2SO4 and concentrate in vacuo. Pass the residue through a small plug of silica gel eluting with hexane/EtOAc (3:1) to provide the desired intermediate as a clear liquid (9.0 g, 81%).

Workup

  1. extractionAdd brine, extract the reaction mixture twice with EtOAc
  2. dry with materialdry the organic layer over anhydrous Na2SO4
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-e3f5cfea4ec54a9cacc5ab3b8aa89d27
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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