4-(2-Propenyl)-2-cyclohexen-1-one → (3R,4S)-3-Methyl-4-(prop-2-en-1-yl)cyclohexan-1-one

HRID 1762246Notes

Reaction equation

HRID 1762246 reaction equation
[Li].[CH3:2][Cu]C.[CH2:5]([CH:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=[CH:9]1)[CH:6]=[CH2:7]>O1CCCC1>[CH3:2][C@H:9]1[C@H:8]([CH2:5][CH:6]=[CH2:7])[CH2:13][CH2:12][C:11](=[O:14])[CH2:10]1

Participants

4

Reactant 2

HCID 109535714-(2-Propenyl)-2-cyclohexen-1-oneHCID 178477771HCID 178477771, compound

Product 1

HCID 15670663(3R,4S)-3-Methyl-4-(prop-2-en-1-yl)cyclohexan-1-oneYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. solution of 0.282 mole of dimethyl copper lithium in 200 ml. of tetrahydrofuran was slowly added a solution of 25.6 g. (0.188 mole) of 4-(2-propenyl)cyclohex-2-en-1-one in 50 ml. of tetrahydrofuran. The reaction was stirred 15 minutes and then quenched by addition to a 0° C. saturated solution (500 ml.) of ammonium chloride. The quenched reaction was extracted with 500 ml. ether. The ether extract was washed with 500 ml. saturated ammonium chloride, dried over magnesium sulfate and evaporated to an oil which was purified via distillation to yield 15.5 g. (55%) of the title compound.

Workup

  1. customTo a 0° C.
  2. customquenched by addition to a 0° C. saturated solution (500 ml.) of ammonium chloride
  3. customThe quenched reaction
  4. extractionwas extracted with 500 ml
  5. extractionThe ether extract
  6. washwas washed with 500 ml
  7. dry with materialsaturated ammonium chloride, dried over magnesium sulfate
  8. customevaporated to an oil which
  9. distillationwas purified via distillation
  10. customto yield 15.5 g

Sources & evidence

ORD record
ord-1217ec41155447f3869d7b2f4b5639da
Source dataset
uspto-grants-1989_05
Patent number
US04831059

Reaction notes

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