Ethyl Acetate → 6-Bromo-3-pyridinemethanol

HRID 889288Notes

Reaction equation

HRID 889288 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[N:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][CH:9]=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:7][C:8]1[N:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 117692346-Bromo-3-pyridinecarboxaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 64212496-Bromo-3-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

1.34 ml (1.34 mmol) of a 1 M solution of lithium aluminum hydride in THF are initially introduced into 5 ml dry THF under argon, and a solution of 500 mg (2.69 mmol) 6-bromo-3-pyridinecarbaldehyde in 3 ml dry THF is added dropwise at 0° C. The mixture is subsequently stirred at RT for 1 h, 25 ml ethyl acetate are then added, while cooling in an ice bath, and hydrolysis is carried out slowly with 50 ml saturated sodium bicarbonate solution. The aqueous phase is extracted with ethyl acetate (three times with 20 ml each time). The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated on a rotary evaporator. After removal of solvent residues in vacuo, 375 mg (74% of th.) of the title compound are obtained.

Workup

  1. temperaturewhile cooling in an ice bath
  2. customhydrolysis
  3. extractionThe aqueous phase is extracted with ethyl acetate (three times with 20 ml each time)
  4. washThe combined organic phases are washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator
  8. customAfter removal of solvent residues in vacuo, 375 mg (74% of th.) of the title compound
  9. customare obtained

Sources & evidence

ORD record
ord-f9177274196542acb3d17037bee44ab9
Source dataset
uspto-grants-2012_08
Patent number
US08252817B2

Reaction notes

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