Benzyl Bromide → [(Cyclopent-3-en-1-yloxy)methyl]benzene

HRID 1416444Notes

Reaction equation

HRID 1416444 reaction equation
[CH:1]1([OH:6])[CH2:5][CH:4]=[CH:3][CH2:2]1.[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH2:7]([O:6][CH:1]1[CH2:5][CH:4]=[CH:3][CH2:2]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 2814783-Cyclopenten-1-ol

Product 1

HCID 11788566[(Cyclopent-3-en-1-yloxy)methyl]benzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cyclopent-3-en-1-ol [cf. J. Org. Chem., 32, 4138 (1967)] (7.00 g) and benzyl bromide (10.5 ml) in dimethylformamide (35 ml) is added gradually 60% sodium hydride (in oil) (3.68 g) with stirring under ice-cooling, and the mixture is stirred at room temperature for 1.5 hour. The reaction mixture is diluted with ethyl acetate and washed with water six times. The ethyl acetate solution thus obtained is dried over anhydrous magnesium sulfate, evaporated to dryness under reduced pressure, and then purified by medium pressure liquid column chromatography (eluent; n-hexane, n-hexane:ethyl acetate--50:1, v/v) to give 4-benzyloxycyclopent-1-ene (11.22 g) as an oily substance.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at room temperature for 1.5 hour
  3. washwashed with water six times
  4. customThe ethyl acetate solution thus obtained
  5. dry with materialis dried over anhydrous magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. custompurified by medium pressure liquid column chromatography (eluent

Sources & evidence

ORD record
ord-e0a9414e096240388b4afe334b8cf33f
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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