Benzyl Alcohol → 2-(Benzyloxy)-4-methylpyridine

HRID 1727343Notes

Reaction equation

HRID 1727343 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=1.O>CCCCCC.O1CCCC1>[C:4]1([CH2:3][O:10][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 27340872-Bromo-4-methylpyridine

Product 1

HCID 142234762-(Benzyloxy)-4-methylpyridineYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

Sodium hydride (60% paraffin dispersion, 5.0 g, 120 mmol) was washed with hexane (5 mL) twice, and suspended in tetrahydrofuran (200 mL). To this suspension was added dropwise a solution of benzyl alcohol (14 g, 120 mol) in tetrahydrofuran (50 mL) at 0° C., and the mixture was allowed to warm to room temperature and stirred for 15 minutes. To this solution was added a solution of 2-bromo-4-methylpyridine (20 mL, 110 mol) in tetrahydrofuran (50 mL), and the mixture was heated to reflux for 14 hours. Water (200 mL) was added to the reaction mixture, and extracted with ethyl acetate. The extracted solution was dried, and the solvent was distilled off. The crude product was distilled under reduced pressure to obtain a title compound (13 g, yield 67%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 14 hours
  3. extractionextracted with ethyl acetate
  4. customThe extracted solution was dried
  5. distillationthe solvent was distilled off
  6. distillationThe crude product was distilled under reduced pressure

Sources & evidence

ORD record
ord-8cc1b29e78524b54bf418745fbe92b36
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

Loading…