Hydrochloric Acid → HCID 66867987, compound

HRID 1631897Notes

Reaction equation

HRID 1631897 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)C1C=CC=CC=1.Cl>CC(C)=O.O>[CH3:1][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:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[CH3:30])[C:18](=[O:31])[CH2:17]/2)[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66868370HCID 66868370, compound

Product 1

HCID 66867987HCID 66867987, compoundYield 23.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-[(4-benzyloxy-cyclohexyl)-hydroxy-methyl]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (1.5 g, 4.0 mmol) in acetone (3 ml) is added 2N aqueous hydrochloric acid (3 ml) and the mixture heated for 1 hour at 120° C. by microwave irradiation. The reaction mixtures is then diluted with water (20 ml) and extracted with ethyl acetate (3×15 ml). The combined organic extracts are dried over magnesium sulfate, filtered and evaporated under reduced pressure to give a brown gum. The gum is purified by flash chromatography eluting with hexane/ethyl acetate to give 4-[1-(4-Methoxy-cyclohexyl)-meth-(E)-ylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione as a colourless solid (0.32 g).

Workup

  1. customThe reaction mixtures
  2. extractionextracted with ethyl acetate (3×15 ml)
  3. dry with materialThe combined organic extracts are dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give a brown gum
  7. customThe gum is purified by flash chromatography
  8. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-918186fe5cfb4e8380ab0735364f7764
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

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