Citric Acid → 1-(6-Bromopyridin-3-yl)-2-methoxyethanol

HRID 1881896Notes

Reaction equation

HRID 1881896 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:12])[CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1.O1CCCC1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:12])[CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 593315581-(6-Bromopyridin-3-yl)-2-methoxyethan-1-one

Product 1

HCID 593315801-(6-Bromopyridin-3-yl)-2-methoxyethanolYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1-(6-bromopyridin-3-yl)-2-methoxyethanone (15.85 g), tetrahydrofuran (15 mL) and ethanol (15 mL) was slowly added sodium borohydride (0.97 g) at room temperature, and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (15.26 g, yield 96%) was obtained as a yellow oil from a fraction eluted with ethyl acetate. MS: 234 (MH+).

Workup

  1. customat room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a5de980d5da344ef97f42271328f69f8
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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