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

HRID 844411Notes

Reaction equation

HRID 844411 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

44 mg of cyclopentenone and 287 mg of t-butyl 2,2,2-trichloroacetimidate (Aldrich, 36,478-9) was dissolved in 2.5 ml of dichloromethane under argon flow. 1 ml of 28 μl/ml boron trifluoride diethyl ether complex 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 to purify 4-t-butylcyclopentenone ether, 5-t-butylcyclopentenone ether and 4,5-di-t-butylcyclopentenone ether as described in Referential Example 1-(21). The Rf values for 4-t-butylcyclopentenone ether, 5-t-butylcyclopentenone ether and 4,5-di-t-butylcyclopentenone ether were 0.35, 0.27 and 0.73, respectively. The yields of 4-t-butylcyclopentenone ether, 5-t-butylcyclopentenone ether and 4,5-di-t-butylcyclopentenone ether were 9.2%, 1.9% and 11%, respectively.

Workup

  1. stirringAfter stirring for 8 hours at room temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customto purify 4-t-butylcyclopentenone ether, 5-t-butylcyclopentenone ether and 4,5-di-t-butylcyclopentenone ether

Sources & evidence

ORD record
ord-1c86bdc9bd244a4d8d8d7e0308b17ba2
Source dataset
uspto-grants-2002_04
Patent number
US06380262B1

Reaction notes

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