Sodium borohydride → (2-Ethoxypyridin-4-yl)methanol

HRID 1169677Notes

Reaction equation

HRID 1169677 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[C:10]([C:12](OCC)=[O:13])[CH:9]=[CH:8][N:7]=1)[CH3:4]>C(O)C.ClCCl>[CH2:3]([O:5][C:6]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][N:7]=1)[CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 13681281Ethyl 2-ethoxypyridine-4-carboxylate

Product 1

HCID 23094032(2-Ethoxypyridin-4-yl)methanolYield 75.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

0.508 g of sodium borohydride is added portionwise to a solution of 0.524 g of ethyl 2-ethoxypyridine-4-carboxylate in 5.2 ml of ethanol, under an inert atmosphere of argon at a temperature in the region of 0° C. The reaction mixture is refluxed with stirring for 3 hours and then concentrated to dryness under reduced pressure. The residue thus obtained is taken up in 50 ml of dichloromethane and then washed with 50 ml of water. The organic phase is dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure. 0.310 g of 2-ethoxy-4-(hydroxymethyl)pyridine is thus obtained.

Workup

  1. temperatureThe reaction mixture is refluxed
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe residue thus obtained
  4. washwashed with 50 ml of water
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-76d8eb81975b4f2b87b344b8c87e398a
Source dataset
uspto-grants-2010_11
Patent number
US07825115B2

Reaction notes

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