2-Cyclopenten-1-one → HCID 69338188, compound

HRID 844410Notes

Reaction equation

HRID 844410 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.Cl[C:8](Cl)(Cl)[C:9](=N)[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[CH2:11]([CH:4]1[CH2:5][C:1](=[O:6])[CH:2]=[CH:3]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:8][CH2:9][O:10][CH2:11][CH3:12].[CH2:11]([CH:5]1[C:1](=[O:6])[CH:2]=[CH:3][CH2:4]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:8][CH2:9][O:10][CH2:11][CH3:12].[CH2:11]([CH:4]1[CH:5]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:1](=[O:6])[CH:2]=[CH:3]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:8][CH2:9][O:10][CH2:11][CH3:12]

Participants

6

Reactant 2

HCID 135882-Cyclopenten-1-oneHCID 144968Benzyl 2,2,2-trichloroacetimidate

Product 3

HCID 69338188HCID 69338188, compoundHCID 69339691HCID 69339691, compoundHCID 69339833HCID 69339833, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

44 mg of cyclopentenone and 492 mg of benzyl 2,2,2-trichloroacetimidate (Aldrich, 14,033-3) was dissolved in 2.5 ml of dichloromethane (Wako Pure Chemical Industries, 135-02441) under argon flow. 1 ml of 28 μl/ml boron trifluoride diethyl ether complex (Wako Pure Chemical Industries, 022-08362) solution in dichloromethane was slowly added thereto while stirring. After stirring for 8 hours at room temperature, the mixture was concentrated under reduced pressure. The concentrate was subjected to silica gel thin-layer chromatography using chloroform:methanol=19:1 as a developing solvent to purify 4-benzylcyclopentenone ether, 5-benzylcyclopentenone ether and 4,5-dibenzylcyclopentenone ether. The Rf values for 4-benzylcyclopentenone ether, 5-benzylcyclopentenone ether and 4,5-dibenzylcyclopentenone ether were 0.3, 0.45 and 0.8, respectively. The yields of 4-benzylcyclopentenone ether, 5-benzylcyclopentenone ether and 4,5-dibenzylcyclopentenone ether were 3.7%, 3.7% and 2.5%, respectively.

Workup

  1. stirringAfter stirring for 8 hours at room temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. custommethanol=19:1 as a developing solvent to purify 4-benzylcyclopentenone ether, 5-benzylcyclopentenone ether and 4,5-dibenzylcyclopentenone ether

Sources & evidence

ORD record
ord-2618f642a39f49a695bb9ef9b394e7ea
Source dataset
uspto-grants-2002_04
Patent number
US06380262B1

Reaction notes

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