Sodium borohydride → 1-(6-Bromopyridin-3-yl)ethane-1,2-diol

HRID 1881838Notes

Reaction equation

HRID 1881838 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:14])[C:9](OCC)=[O:10])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:14])[CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 46941438Ethyl 2-(6-bromopyridin-3-yl)-2-oxoacetate

Product 1

HCID 469414371-(6-Bromopyridin-3-yl)ethane-1,2-diolYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl (6-bromopyridin-3-yl)(oxo)acetate (1.00 g) in ethanol (20 mL) was slowly added sodium borohydride (250 mg). The reaction mixture was stirred at room temperature for 4 hr, diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give the title compound (650 mg, yield 77%) as a colorless oil. MS: 220 (MH+).

Workup

  1. washwashed with water
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-acb1dd40ca2249f98f12b42aa3d02dc3
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…