Sodium borohydride → (5-Bromopyridin-2-yl)methanol

HRID 861004Notes

Reaction equation

HRID 861004 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[BH4-].[Na+]>C1COCC1.CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 98775625-Bromopyridine-2-carbaldehyde

Product 1

HCID 5200169(5-Bromopyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-bromo-pyridine-2-carbaldehyde (1.0 eq.) in THF:EtOH (1:1; 0.2M) at −78° C. was added NaBH4 (4.0 eq.). The mixture was stirred for 2 h at −78° C., quenched with excess AcOH, poured in aqueous HCl (1M), stirred for 15 min, neutralized to pH=7 with NaOH (1M) and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound as an oil.

Workup

  1. customquenched with excess AcOH
  2. additionpoured in aqueous HCl (1M)
  3. stirringstirred for 15 min
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-de8769aa25fe4cc88d28a7f4157852fa
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

Loading…