Sodium borohydride → 1-(6-Bromo-2-pyridinyl)ethanol

HRID 385756Notes

Reaction equation

HRID 385756 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.ClCCl.O>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 112985782-Acetyl-6-bromopyridine

Product 1

HCID 110634791-(6-Bromo-2-pyridinyl)ethanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(6-bromopyridin-2-yl)ethanone (2.9636 g, 14.82 mmol) in methanol (40 mL) at 0° C. was charged with sodium borohydride (1.682 g, 44.4 mmol) and then allowed to warm to room temperature. After 2.5 hours, the reaction mixture was diluted with dichloromethane (60 mL) and water (60 mL) and the layers were separated. The organic layer was dried over sodium sulfate, filtered, and concentrated to yield the title compound.

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7d668943413840dabfbdd461a0cf7016
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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