HCID 67388428, compound → HCID 58444072, compound

HRID 1965831Notes

Reaction equation

HRID 1965831 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][C:14](=[CH:21][C:22]2([CH2:28][CH3:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[C:15]3=[O:20])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][CH:14]([CH2:21][C:22]2([CH2:28][CH3:29])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[C:15]3=[O:20])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 67388428HCID 67388428, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 58444072HCID 58444072, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

25.0 g of crude 4-(4-tert-butyl-phenyl)-2-(1-ethylcyclo-hexylmethylene)-indan-1-one (GC: ˜83% purity) are dissolved in 250 ml of ethyl acetate in a flask with gas inlet and stirrer. 1.75 g of palladium on activated carbon (10 wt-% palladium) are added. The system is evacuated and refilled with argon three times to remove oxygen and then evacuated and refilled with hydrogen three times. The stirrer is started and the reaction mixture is vigorously stirred to help the diffusion of hydrogen gas into the liquid reaction mixture. The hydrogen uptake is monitored and stirring is continued until the hydrogen uptake ceases. Filtering the crude reaction mixture over a paper filter and removing the solvent in a vacuum leaves crude 4-(4-tert-butyl-phenyl)-2-(1-ethyl-cyclohexylmethyl)-indan-1-one (yield 24.4 g, GC: ˜82% purity). The obtained crude product was used without further purification for the subsequent reduction/elimination-sequence.

Workup

  1. customThe system is evacuated
  2. additionrefilled with argon three times
  3. customto remove oxygen
  4. customevacuated
  5. additionrefilled with hydrogen three times
  6. custominto the liquid reaction mixture
  7. stirringstirring
  8. filtrationFiltering the crude
  9. customreaction mixture over a paper
  10. filtrationfilter
  11. customremoving the solvent in a vacuum

Sources & evidence

ORD record
ord-de3962b84f134e46aca96d0a52066ea9
Source dataset
uspto-grants-2013_04
Patent number
US08415492B2

Reaction notes

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