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

HRID 2212328Notes

Reaction equation

HRID 2212328 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 mmol) in tetrahydrofuran (50 mL) at 0° C. and then, the mixture was allowed to warm up to room temperature with stirring for 15 minutes. To this solution was added a solution of 2-bromo-4-methylpyridine (19.5 mL, 110 mmol) in tetrahydrofuran (50 mL) and heated to reflux for 14 hours. To the reaction mixture was added water (200 mL) and extracted with ethyl acetate. The extract was dried and the solvent was distilled off. The crude product was distilled under reduced pressure to obtain 13 g of the title compound (67 mmol, yield 67%).

Workup

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

Sources & evidence

ORD record
ord-d68083726e9b4b8792728e518284571f
Source dataset
uspto-grants-2006_09
Patent number
US07101899B1

Reaction notes

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