6-Oxabicyclo[3.1.0]hexane → 38805-90-2

HRID 989481Notes

Reaction equation

HRID 989481 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9]12[O:14][CH:10]1[CH2:11][CH2:12][CH2:13]2>C1COCC1.[Cu](I)I>[C:1]1([C@@H:9]2[CH2:13][CH2:12][CH2:11][C@H:10]2[OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 92446-Oxabicyclo[3.1.0]hexaneHCID 178418255HCID 178418255, compound

Product 1

HCID 1089900638805-90-2

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

Scheme IB, step A: A one liter three necked round bottom flask equipped with a mechanical stirrer, addition funnel, thermometer is charged with 1M THF solution of phenylmagnesium bromide (300 mL, 300.0 mmol) and copper iodide (3.8 g, 20.0 mmol). To this reaction mixture was then added cyclopentene oxide (25.23 g, 300.0 mmol) dissolved in THF (50.0 mL) dropwise over a period of 60 minutes (reaction was quite exothermic, reaching THF reflux by the end of addition). The reaction mixture was then stirred to room temperature and quenched with 25% solution of ammonium chloride (200.0 mL). Added ether (80.0 mL) and separated upper organic layer. Washed organic layer with 25% ammonium chloride solution, dried with anhydrous magnesium sulfate, filtered and concentrated filtrate to provide (+,−) trans-2-phenyl-cyclopentanol as a brown oil (mass =47.7 g);

Workup

  1. customreaction
  2. temperaturereflux by the end of addition)
  3. customquenched with 25% solution of ammonium chloride (200.0 mL)
  4. customAdded ether (80.0 mL) and separated upper organic layer
  5. dry with materialWashed organic layer with 25% ammonium chloride solution, dried with anhydrous magnesium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-3d8b80a3b59e4702ae8ee2f6d81f0437
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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