Pyridine → (1S)-4-Oxocyclopent-2-en-1-yl benzoate

HRID 2163164Notes

Reaction equation

HRID 2163164 reaction equation
[C:1]([O:9][C@H:10]1[CH2:14][C@H:13]([OH:15])[CH:12]=[CH:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1CC(=O)C=C1)(=O)C.N1C=CC=CC=1>C(Cl)Cl>[C:1]([O:9][C@H:10]1[CH2:14][C:13](=[O:15])[CH:12]=[CH:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 3431174-Oxocyclopent-2-en-1-yl acetateHCID 23583487(S)-trans-3-benzoyloxy-5-hydroxycyclopent-1-ene

Product 1

HCID 14569885(1S)-4-Oxocyclopent-2-en-1-yl benzoateYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

38 milligrams of the (S)-trans-3-benzoyloxy-5-hydroxycyclopent-1-ene obtained by the method of (1), above, was added in 15 milliliters of methylene chloride to a chromic acid-pyridine complex prepared from 100 milligrams of chromic anhydride and 159 milligrams of pyridine, following which the mixture was stirred for 20 minutes at room temperature. The organic layer was then separated, successively washed in a 5% aqueous NaOH solution, 5% aqueous HCl solution and water and dried, after which the solvent was distilled off to obtain 22 milligrams of 4(S)-benzoyloxycyclopent-2-en-1-one having a Δε226 = -14° and exhibiting the same IR, NMR and mass as those of the product obtained in Example 9. The yield was 58%.

Workup

  1. customThe organic layer was then separated
  2. washsuccessively washed in a 5% aqueous NaOH solution, 5% aqueous HCl solution and water
  3. customdried
  4. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-e300ea9c25144511af0cb157aa332d9b
Source dataset
uspto-grants-1979_01
Patent number
US04132726

Reaction notes

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