Lithium Chloride → 5-Chloro-2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone

HRID 407836Notes

Reaction equation

HRID 407836 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:19])[CH2:14][CH2:15][C:16]=1[O:17][CH3:18])[CH3:2].[Cl-:20].[Li+]>O1CCOCC1.[Cu](Cl)Cl>[Cl:20][CH:14]1[C:13](=[O:19])[C:12]([C:4]2[C:5]([CH2:10][CH3:11])=[CH:6][C:7]([CH3:9])=[CH:8][C:3]=2[CH2:1][CH3:2])=[C:16]([O:17][CH3:18])[CH2:15]1

Participants

5

Reactant 2

HCID 433294Lithium ChlorideHCID 672833702-(2,6-Diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone

Product 1

HCID 672841155-Chloro-2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone (0.715 g, 2.77 mmol) in 1,4-dioxane (45 ml), and under an atmosphere of nitrogen, are added copper (II) chloride (0.743 g, 5.53 mmol) and lithium chloride (0.176 g, 4.15 mmol). The reaction is heated at reflux for 7 hours and allowed to cool to room temperature overnight. The remaining solid is removed by filtration and washed with ethyl acetate (50 ml). The filtrate is washed with water (2×25 ml) and the aqueous washings re-extracted with ethyl acetate (1.5 ml). The combined organic phases are washed with brine (15 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure to give a brown oil. The crude product is purified by column chromatography on silica gel to give 5-chloro-2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone.

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux for 7 hours
  3. customThe remaining solid is removed by filtration
  4. washwashed with ethyl acetate (50 ml)
  5. washThe filtrate is washed with water (2×25 ml)
  6. extractionthe aqueous washings re-extracted with ethyl acetate (1.5 ml)
  7. washThe combined organic phases are washed with brine (15 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe filtrate is evaporated under reduced pressure
  11. customto give a brown oil
  12. customThe crude product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-726433510c684db2bd9c5b91a8345e47
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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