Benzyl Bromide → HCID 21955250, compound

HRID 2213010Notes

Reaction equation

HRID 2213010 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=1.[BH4-].[Na+]>CC(C)=O>[C:2]1([CH2:1][N:9]2[CH2:10][CH:11]=[C:12]([CH2:15][CH2:16][OH:17])[CH2:13][CH2:14]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 729214-PyridineethanolHCID 4311764Sodium borohydride

Product 1

HCID 21955250HCID 21955250, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyl bromide (4.4 mL, 41 mmol) was added to a solution of 4-pyridineethanol (5 g, 41 mmol) in acetone (100 mL) and the mixture was heated under reflux for 16 hours. The mixture was cooled and the solid was collected, washed with acetone (50 mL) and diethyl ether (2×50 mL) then dissolved in methanol (100 mL) and treated with sodium borohydride (6.2 g 164 mmol). The mixture was heated under reflux for 16 hours, cooled, and the solvent was evaporated under reduced pressure. Ethyl acetate (200 mL) and aqueous sodium hydrogen carbonate (10%, 150 mL) were added and the layers were separated. The aqueous layer was extracted with ethyl acetate (2×100 mL), the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2/MeOH/NH3(Aq.) (92:8:1), to give the title compound as a colorless oil (1.65 g, 18%). m/z (ES+) 218 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. temperatureThe mixture was cooled
  4. customthe solid was collected
  5. washwashed with acetone (50 mL) and diethyl ether (2×50 mL)
  6. dissolutionthen dissolved in methanol (100 mL)
  7. temperatureThe mixture was heated
  8. temperatureunder reflux for 16 hours
  9. temperaturecooled
  10. customthe solvent was evaporated under reduced pressure
  11. additionEthyl acetate (200 mL) and aqueous sodium hydrogen carbonate (10%, 150 mL) were added
  12. customthe layers were separated
  13. extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
  14. dry with materialthe combined organic fractions were dried (MgSO4)
  15. customthe solvent was evaporated under reduced pressure
  16. customThe residue was purified by flash column chromatography on silica gel
  17. washeluting with CH2Cl2/MeOH/NH3(Aq.) (92:8:1)

Sources & evidence

ORD record
ord-645291b3b74c4e0897909af6000bb401
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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