2-(4-Bromo-2,6-dimethyl-phenyl)-5-(cyclohexyl-hydroxy-methyl)-3-methoxy-cyclopent-2-enone → 2-(4-bromo-2,6-dimethyl-phenyl)-4-[1-cyclohexyl-meth-(E)-ylidene]-cyclopentane-1,3-dione

HRID 1631882Notes

Reaction equation

HRID 1631882 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:10](=[O:24])[CH:11]([CH:16]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)O)[CH2:12][C:13]=2[O:14]C)=[C:4]([CH3:25])[CH:3]=1>C(O)C.Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH3:25])[C:5]([CH:9]2[C:10](=[O:24])/[C:11](=[CH:16]/[CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)/[CH2:12][C:13]2=[O:14])=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 1

HCID 668685772-(4-Bromo-2,6-dimethyl-phenyl)-5-(cyclohexyl-hydroxy-methyl)-3-methoxy-cyclopent-2-enone

Product 1

HCID 668680902-(4-bromo-2,6-dimethyl-phenyl)-4-[1-cyclohexyl-meth-(E)-ylidene]-cyclopentane-1,3-dioneYield 19.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 2-(4-bromo-2,6-dimethyl-phenyl)-5-(cyclohexyl-hydroxy-methyl)-3-methoxy-cyclopent-2-enone (1.38 g, 3.4 mmol) in ethanol (27.6 ml) and 2N aqueous hydrochloric acid (13.8 ml) is subjected to microwave irradiation at 130° C. for 40 minutes. The reaction mixture is concentrated under vacuum to remove ethanol. The aqueous layer was extracted with ethyl acetate (3×100 ml) and combined organic layers are dried with sodium sulfate and concentrated under vacuum to obtain crude mass. The compound was purified by column chromatography to give 2-(4-bromo-2,6-dimethyl-phenyl)-4-[1-cyclohexyl-meth-(E)-ylidene]-cyclopentane-1,3-dione (250 mg).

Workup

  1. customirradiation at 130° C. for 40 minutes
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. customto remove ethanol
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×100 ml)
  5. dry with materialare dried with sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customto obtain crude mass
  8. customThe compound was purified by column chromatography

Sources & evidence

ORD record
ord-6f236b47e799460bb81928685550b6b1
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

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