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

HRID 2092829Notes

Reaction equation

HRID 2092829 reaction equation
[CH:1]1([OH:6])[CH2:5][CH:4]=[CH:3][CH2:2]1.[H-].[Na+].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[CH:1]1([O:6][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

5

Reactant 3

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

Product 1

HCID 11788566[(Cyclopent-3-en-1-yloxy)methyl]benzeneYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution of cyclopent-3-enol (30.40 g, 0.36 mol) in THF (300 mL) at 0° C. was added NaH (18.82 g, 0.47 mol, 60% in mineral oil). After effervescence had ceased, benzyl bromide (80.45 g, 0.47 mol) was added dropwise at 0° C. over a 45 min period. The reaction mixture was allowed to warm to RT over a 6 h period. Excess NaH was quenched with MeOH (120 mL) at a temperature below 5° C. The mixture was warmed to RT, diluted with H2O, and the two layers were separated. The aqueous layer was extracted with EtOAc. The organic layers were combined, concentrated, and purified by column chromatography eluting with petroleum ether and EtOAc (PE/EA=40/1 to 30/1) to give the title compound as an oil (45.28 g, 72%). 1H NMR (400 MHz, CDCl3) δ ppm 2.38-2.41 (m, 2H), 2.49-2.54 (m, 2H), 4.20-4.24 (m, 1H), 4.42 (s, 2H), 5.62 (s, 2H), 7.17-7.28 (m, 5H).

Workup

  1. customExcess NaH was quenched with MeOH (120 mL) at a temperature below 5° C
  2. temperatureThe mixture was warmed to RT
  3. additiondiluted with H2O
  4. customthe two layers were separated
  5. extractionThe aqueous layer was extracted with EtOAc
  6. concentrationconcentrated
  7. custompurified by column chromatography
  8. washeluting with petroleum ether and EtOAc (PE/EA=40/1 to 30/1)

Sources & evidence

ORD record
ord-a2b50ee0a0f24e718f9d9335dfaa128d
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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