Cyclopentene → Ethyl 3-cyclopenten-1-ylbenzoate

HRID 1767759Notes

Reaction equation

HRID 1767759 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:13]1[CH2:17][CH2:16][CH2:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].C(O)C>[C:13]1([C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:17][CH2:16][CH2:15][CH:14]=1

Participants

6

Reactant 3

HCID 8882CyclopenteneHCID 11430Potassium CarbonateHCID 143542Ethyl 3-iodobenzoate

Product 1

HCID 12094926Ethyl 3-cyclopenten-1-ylbenzoate

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

The following are successively introduced into a round-bottomed flask: 7 g of ethyl 3-iodobenzoate (25 mmol), 11.2 ml of cyclopentene (127 mmol), 21 ml of ethanol, 1.16 g of Pd2dba3 complex (1.27 mmol), 8.8 g of potassium carbonate (63 mmol) and 8.17 g of nBu4NBr (25 mmol). The medium is heated at 80° C. for 16 hours and then the black mixture is filtered on celite. The precipitate is washed with ethyl acetate. The filtrate is washed with water and then with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The title product, which is isolated by bulb to bulb distillation (5.2 g), is obtained in the form of a pale yellow oil.

Workup

  1. additionThe following are successively introduced into a round-bottomed flask
  2. filtrationthe black mixture is filtered on celite
  3. washThe precipitate is washed with ethyl acetate
  4. washThe filtrate is washed with water
  5. dry with materialwith a saturated aqueous sodium chloride solution, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1390fa391864490eb5ecd8fae029f29d
Source dataset
uspto-grants-2007_06
Patent number
US07235568B2

Reaction notes

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