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

HRID 706651Notes

Reaction equation

HRID 706651 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]1[N:11]=[C:10]([C:12](OCC)=[O:13])[CH:9]=[CH:8][CH:7]=1)[CH3:4]>CCO>[CH2:3]([O:5][C:6]1[N:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][CH:7]=1)[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53393170Ethyl 6-ethoxypyridine-2-carboxylate

Product 1

HCID 53393171(6-Ethoxypyridin-2-yl)methanolYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (16.0 g, 424 mmol) was added in portions over 35 minutes to ethyl 6-ethoxypicolinate (4.14 g, 21.2 mmol) in EtOH (0.2M, 200 mL). The resulting mixture was stirred at ambient temperature for two days. The mixture was concentrated and the residue was distributed between water and DCM. The organic layer was dried (phase separator silicone treated filter paper), and concentrated to give (6-ethoxypyridin-2-yl)methanol (3.05 g, 94% yield) as a pale yellow oil.

Workup

  1. concentrationThe mixture was concentrated
  2. customThe organic layer was dried
  3. addition(phase separator silicone treated filter paper)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d1262748f82e4423815b0d9e3d6de82e
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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