Hydrochloric Acid → 4-[1-Cycloheptyl-methylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione

HRID 1631890Notes

Reaction equation

HRID 1631890 reaction equation
[CH:1]1([CH:8](O)[CH:9]2[C:13](=[O:14])[C:12]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])=[C:11]([O:24]C)[CH2:10]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>CC(C)=O.O>[CH:1]1([CH:8]=[C:9]2[CH2:10][C:11](=[O:24])[CH:12]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:13]2=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 668682975-(Cycloheptyl-hydroxy-methyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone

Product 1

HCID 668683574-[1-Cycloheptyl-methylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dioneYield 96.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 5-(Cycloheptyl-hydroxy-methyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (100 mg, 0.28 mmol) in acetone (4 ml) in a 10 ml vial was added 2M HCl (4 ml). The reaction was capped and heated to 120 C for 30 minutes under microwave irradiation. The reaction was diluted with H2O (20 ml) and extracted with EtOAc (3×15 ml). The combined organic extracts were washed with brine (10 ml), dried over MgSO4, filtered and evaporated to dryness under reduced pressure to give a brown oil (88 mg). The crude material was purified by flash chromatography over SiO2 using a 100% isohexane to 100% EtOAc gradient to give the desired product as a colourless oil (62 mg).

Workup

  1. customThe reaction was capped
  2. temperatureheated to 120 C for 30 minutes under microwave irradiation
  3. extractionextracted with EtOAc (3×15 ml)
  4. washThe combined organic extracts were washed with brine (10 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-edd2fe3ea1c0415dbab46a82eedec842
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

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