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

HRID 1169679Notes

Reaction equation

HRID 1169679 reaction equation
[BH4-].[Na+].[CH2:3]([C:5]1[CH:10]=[C:9]([C:11](OCC)=[O:12])[CH:8]=[CH:7][N:6]=1)[CH3:4]>C(O)C.ClCCl>[CH2:3]([C:5]1[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[CH:7][N:6]=1)[CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 53434474HCID 53434474, compound

Product 1

HCID 9964106(2-Ethylpyridin-4-yl)methanolYield 81.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

5.36 g of sodium borohydride are added portionwise to a solution of 5.08 g of ethyl 2-ethylpyridine-4-carboxylate in 53 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 500 ml of dichloromethane and then washed with 500 ml of water. The organic phase is dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure. 3.16 g of 2-ethyl-4-(hydroxymethyl)pyridine are thus obtained.

Workup

  1. temperatureThe reaction mixture is refluxed
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe residue thus obtained
  4. washwashed with 500 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-0bafa7e1c7f746ca84aeb4de692666a7
Source dataset
uspto-grants-2010_11
Patent number
US07825115B2

Reaction notes

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