2-Cyclopenten-1-one → HCID 69338281, compound

HRID 1873110Notes

Reaction equation

HRID 1873110 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][C:11]([CH3:14])([CH3:13])[CH3:12]>ClCCl>[C:11]([CH:4]1[CH2:5][C:1](=[O:6])[CH:2]=[CH:3]1)([CH3:14])([CH3:13])[CH3:12].[CH3:8][CH2:9][O:10][CH2:11][CH3:12].[C:11]([CH:5]1[C:1](=[O:6])[CH:2]=[CH:3][CH2:4]1)([CH3:14])([CH3:13])[CH3:12].[CH3:8][CH2:9][O:10][CH2:11][CH3:12].[C:11]([CH:4]1[CH:5]([C:11]([CH3:12])([CH3:13])[CH3:14])[C:1](=[O:6])[CH:2]=[CH:3]1)([CH3:14])([CH3:13])[CH3:12].[CH3:8][CH2:9][O:10][CH2:11][CH3:12]

Participants

6

Reactant 2

HCID 135882-Cyclopenten-1-oneHCID 2734700Tert-butyl 2,2,2-trichloroethanimidate

Product 3

HCID 69338281HCID 69338281, compoundHCID 69339495HCID 69339495, compoundHCID 69339693HCID 69339693, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyclopentenone (44 mg) and 287 mg of tert-butyl 2,2,2-trichloroacetimidate (manufactured by Aldrich, 36,478-9) were dissolved in 2.5 ml of dichloromethane in an argon stream. To this was gradually added 1 ml of a solution of 28 μl/ml of boron trifluoride-diethyl ether complex in dichloromethane with stirring. The mixture was stirred at room temperature for eight hors, concentrated in vacuo and subjected to a silica gel thin layer chromatography by the same manner as in Example 1- (2) to purify 4-tert-butylcyclopentenone ether, 5-tert-butylcyclopentenone ether and 4,5-di-tert-butylcyclopentenone ether. The Rf values of 4-tert-butylcyclopentenone ether, 5-tert-butylcyclopentenone ether and 4,5-di-tert-butylcyclopentenone ether were 0.35, 0.27 and 0.73, respectively. Yields of 4-tert-butylcyclopentenone ether, 5-tert-butylcyclopentenone ether and 4,5-di-tert-butylcyclopentenone ether were 9.2%, 1.9% and 11%, respectively.

Workup

  1. stirringThe mixture was stirred at room temperature for eight hors
  2. concentrationconcentrated in vacuo
  3. customto purify 4-tert-butylcyclopentenone ether, 5-tert-butylcyclopentenone ether and 4,5-di-tert-butylcyclopentenone ether

Sources & evidence

ORD record
ord-21329f0c190f4c0d9c28b77485965532
Source dataset
uspto-grants-2000_08
Patent number
US06111145

Reaction notes

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