Potassium Acetate → 3-Cyclopentylbicyclo[3.2.0]hept-3-en-6-one

HRID 551656Notes

Reaction equation

HRID 551656 reaction equation
C([O-])(=O)C.[K+].O[CH:7]([CH:12]([CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[CH2:13][CH:14]=[CH2:15])[CH2:8][C:9]([OH:11])=O>C(OC(=O)C)(=O)C>[CH:16]1([C:12]2[CH2:13][CH:14]3[CH:8]([CH:7]=2)[C:9](=[O:11])[CH2:15]3)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 67198011HCID 67198011, compound

Product 1

HCID 671994463-Cyclopentylbicyclo[3.2.0]hept-3-en-6-one

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Potassium acetate (4.16 g, 42.4 mmol) was added to an acetic anhydride (20 mL) solution of 3-hydroxy-4-cyclopentylhept-6-enoic acid (4.00 g, 17.7 mmol at the maximum), and the mixture was stirred at room temperature for 1 hour and then stirred at 120° C. for 3.5 hours. The mixture was treated with ice water, followed by extraction with diethyl ether. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the compound of interest as a yellow oil substance (2.30 g, 74%).

Workup

  1. stirringstirred at 120° C. for 3.5 hours
  2. extractionfollowed by extraction with diethyl ether
  3. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. customto obtain the compound of interest as a yellow oil substance (2.30 g, 74%)

Sources & evidence

ORD record
ord-e676a1dede5542dd88888f1dabfdc113
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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