Sodium borohydride → 1-(5-Bromopyridin-2-yl)ethanol

HRID 1501109Notes

Reaction equation

HRID 1501109 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:10])[CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 231453451-(5-Bromopyridin-2-yl)ethan-1-one

Product 1

HCID 426142881-(5-Bromopyridin-2-yl)ethanolYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(5-bromopyridin-2-yl)ethanone (1.1 g, 5.5 mmol) in ethanol (100 mL) was added sodium borohydride (2.5 g, 66.1 mmol). The reaction mixture was stirred at room temperature for 24 hours. The mixture was filtered, the filtrate was acidified and the solvent removed on a rotary evaporator. The residue was taken up with water (50 mL) and extracted with dichloromethane (50 mL). The combined extract was dried over sodium sulfate, filtered, concentrated and purified by column chromatography to give 1-(5-bromopyridin-2-yl)ethanol (1.0 g, 90.0%) as a yellow oil. LRMS (M+H+) m/z: calcd 201.98. found 202. 1H NMR (300 MHz, CD3OD) δ 8.54 (d, J=2.4 Hz, 1H), 7.98 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 7.50 (d, J=8.4 Hz, 1H), 4.85 (m, 1H), 1.45 (d, J=6.6 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent removed on a rotary evaporator
  3. extractionextracted with dichloromethane (50 mL)
  4. extractionThe combined extract
  5. dry with materialwas dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-8b24fbd6904b4b5787ece5fd6c5195c1
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…