HCID 67388651, compound → HCID 58444081, compound

HRID 1965829Notes

Reaction equation

HRID 1965829 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([CH3:28])[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([CH3:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[C:15]3=[O:20])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 67388651HCID 67388651, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 58444081HCID 58444081, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

21.0 g of crude 4-(4-tert-butyl-phenyl)-2-(1-methyl-cyclo-hexylmethylene)-indan-1-one (GC: ˜83% purity) are dissolved in 220 ml of ethyl acetate in a flask with gas inlet and stirrer. 1.5 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-methylcyclohexyl)methyl)-indan-1-one (yield 19.9 g, GC: ˜86% 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-ceeae8ffdb9145b9add7d2b569608dea
Source dataset
uspto-grants-2013_04
Patent number
US08415492B2

Reaction notes

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