Benzyl Bromide → [5-(Benzyloxy)pent-1-en-1-yl]benzene

HRID 1381367Notes

Reaction equation

HRID 1381367 reaction equation
[H-].[Na+].[C:3]1([CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[CH2:15]([O:14][CH2:13][CH2:12][CH2:11][CH:10]=[CH:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1288335-Phenyl-4-pentenol

Product 1

HCID 53797305[5-(Benzyloxy)pent-1-en-1-yl]benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (50%; 0.6 g) (deprived of mineral oil) in tetrahydrofuran (10 ml), there was added dropwise a solution of 5-phenyl-4-pentenol [1.66 g; known compound; cf. e.g. Journal of the Chemical Society, page 1863 (1961)] in tetrahydruforan (10 ml) in argon atmosphere at room temperature. The mixture was stirred at the same temperature for 5 minutes. A solution of benzyl bromide (1.93 g) in tetrahydrofuran (10 ml) was added dropwise and the mixture was stirred at the same temperature for 20 hours. The tetrahydrofuran was distilled off under reduced pressure and water was added to the residue, followed by extraction with ether. After washing with water and drying over magnesium sulfate, the solvent was distilled off, and the residue was subjected to silica gel chromatography, elution being carried out with chlorofrom to give 5-benzyloxy-1-phenyl-1-pentene (2.5 g) as a colorless oil.

Workup

  1. customat room temperature
  2. stirringthe mixture was stirred at the same temperature for 20 hours
  3. distillationThe tetrahydrofuran was distilled off under reduced pressure and water
  4. additionwas added to the residue
  5. extractionfollowed by extraction with ether
  6. washAfter washing with water
  7. dry with materialdrying over magnesium sulfate
  8. distillationthe solvent was distilled off
  9. washthe residue was subjected to silica gel chromatography, elution

Sources & evidence

ORD record
ord-e6b952aa9a6b4efbba43acc8c2c51929
Source dataset
uspto-grants-1986_04
Patent number
US04585789

Reaction notes

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