Benzyl Bromide → (3-(Benzyloxy)pyridin-2-yl)methanol

HRID 2395066Notes

Reaction equation

HRID 2395066 reaction equation
Cl.[OH:2][C:3]1[C:4]([CH2:9][OH:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[OH-].[K+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[CH2:13]([O:2][C:3]1[C:4]([CH2:9][OH:10])=[N:5][CH:6]=[CH:7][CH:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 30841853-Hydroxy-2-(hydroxymethyl)pyridine hydrochloride

Product 1

HCID 13217540(3-(Benzyloxy)pyridin-2-yl)methanolYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 3-hydroxy-2-hydroxymethylpyridine hydrochloride (7.0 g, 12.4 mmol) in ethanol (37.5 ml) was added a solution of KOH pellets (85% 1.6 g, 24.7 mmol) in ethanol (25 ml). The reaction was stirred for 5 minutes at ambient temperature and then benzyl bromide was added (2.11 g, 12.36 mmol). The reaction mixture was stirred at ambient temperature for 48 hours, filtered and evaporated. The residue was purified by chromatography (EtOAc, CH2Cl2) to give 3-benzyloxy-2-hydroxymethylpyridine as a colourless solid (1.55 g, 58%) [J. Med. Chem., 15, (1972) 615] m.p. 78.7°-79.2° C.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 48 hours
  2. filtrationfiltered
  3. customevaporated
  4. customThe residue was purified by chromatography (EtOAc, CH2Cl2)

Sources & evidence

ORD record
ord-4d3b7e4a27ab4aee99ee6ce4a7859d50
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

Loading…