HCID 66868370, compound → HCID 66868058, compound

HRID 1631876Notes

Reaction equation

HRID 1631876 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH:15](O)[CH:16]2[C:20](=[O:21])[C:19]([C:22]3[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[CH3:30])=[C:18]([O:31]C)[CH2:17]2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(C)=O.Cl.O>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12](/[CH:15]=[C:16]2/[C:20](=[O:21])[CH:19]([C:22]3[C:23]([CH3:30])=[CH:24][C:25]([CH3:29])=[CH:26][C:27]=3[CH3:28])[C:18](=[O:31])[CH2:17]/2)[CH2:11][CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 66868370HCID 66868370, compound

Product 1

HCID 66868058HCID 66868058, compoundYield 469.2%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Into six 20 ml microwave vials is added the 5-[(4-benzyloxy-cyclohexyl)-hydroxy-methyl]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (1 g, 2.2 mmol) in a mixture of acetone (7.5 ml) and 2N aqueous hydrochloric acid (7.5 ml). Each vial is therefore heated for 1 hour to 120° C. by microwave irradiation. The reaction mixtures were then combined and diluted with water (100 ml) and extracted with dichloromethane (2×50 m). The combined organic extracts are dried over magnesium sulphate, filtered and evaporated under reduced pressure to give a yellow gum. The gum is purified by flash chromatography to give 4-[1-(4-benzyloxy-cyclohexyl)-meth-(E)-ylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione (4.3 g).

Workup

  1. temperatureEach vial is therefore heated for 1 hour to 120° C. by microwave irradiation
  2. customThe reaction mixtures
  3. extractionextracted with dichloromethane (2×50 m)
  4. dry with materialThe combined organic extracts are dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give a yellow gum
  8. customThe gum is purified by flash chromatography

Sources & evidence

ORD record
ord-e28f47172f644962a65ddb084ec32fe0
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

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