Sodium borohydride → 2-(6-Methoxypyridin-2-yl)ethan-1-ol

HRID 535666Notes

Reaction equation

HRID 535666 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[C:9]([CH2:11][C:12](OCC)=[O:13])[CH:8]=[CH:7][CH:6]=1>C(O)C>[CH3:3][O:4][C:5]1[N:10]=[C:9]([CH2:11][CH2:12][OH:13])[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 55263200Ethyl 2-(6-methoxypyridin-2-YL)acetate

Product 1

HCID 153198712-(6-Methoxypyridin-2-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (1.3 g, 34.8 mmol) was added to a solution of ethyl 2-(6-methoxypyridin-2-yl)acetate (0.68 g, 3.48 mmol) in ethanol (20 mL). The resulting solution was stirred at room temperature over night. The solvent was removed in vacuo. Ethyl acetate and saturated NaHCO3 solution were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated to give the product. Yield: 0.23 g (44%).

Workup

  1. customThe solvent was removed in vacuo
  2. additionEthyl acetate and saturated NaHCO3 solution were added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated
  7. customto give the product

Sources & evidence

ORD record
ord-6580ffdd5e6b405c92aec2bef7c66149
Source dataset
uspto-grants-2014_10
Patent number
US08859534B2

Reaction notes

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