2,4-Dimethylpenta-1,3-diene → HCID 178443936, compound

HRID 1446369Notes

Reaction equation

HRID 1446369 reaction equation
[CH3:1][C:2]([CH:4]=[C:5]([CH3:7])[CH3:6])=[CH2:3].O.[Ru:9](Cl)(Cl)Cl.[CH3:13][C:14]1[CH2:18][CH:17]=[C:16]([CH3:19])[CH:15]=1>CO>[CH3:3][C:2]1([Ru:9][CH:17]=[C:16]([CH3:19])[CH:15]=[C:14]([CH3:13])[CH3:18])[CH:1]=[CH:6][C:5]([CH3:7])=[CH:4]1

Participants

5

Reactant 3

HCID 660802,4-Dimethylpenta-1,3-dieneHCID 6093376Ruthenium trichloride hydrateHCID 111370941,3-dimethylcyclopentadiene

Product 1

HCID 178443936HCID 178443936, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A dry 1 liter 3-neck round-bottom flask was charged with a magnetic stir bar and equipped with three septa. A nitrogen purge was introduced through a needle with output, also via a needle, to an oil bubbler. A thermocouple lead was placed through a side neck septa. Excess zinc (150 grams, ‘dust’ was found more conducive to stirring) was added to the flask. By syringe, 2,4-dimethyl-1,3-pentadiene (25 grams, 0.26 mol) was added to the flask. By cannula, ruthenium trichloride hydrate (6.0 grams, 0.023 mol based on 3 hydrate equivalents) was added as a methanol (250 milliliters) solution in spurts of about 10 milliliters over 45 minutes. The mixture was stirred for 30 minutes at 25° C. after the addition was complete, then, upon equipping a condenser, the contents were brought to gentle reflux. Stirring was continued for 2 hours. The mixture was cooled to 25° C., followed by the addition of freshly distilled 1,3-dimethylcyclopentadiene (2.2 grams, 0.023 mol) by syringe over 20 minutes. Stirring was continued at 25° C. for 20 additional minutes, followed by gentle reflux for 2 hours.

Workup

  1. additionA dry 1 liter 3-neck round-bottom flask was charged with a magnetic stir bar
  2. customequipped with three septa
  3. customA nitrogen purge
  4. additionwas introduced through a needle with output, also via a needle, to an oil bubbler
  5. customA thermocouple lead was placed through a side neck
  6. additionwas added to the flask
  7. stirringThe mixture was stirred for 30 minutes at 25° C.
  8. additionafter the addition
  9. stirringStirring
  10. stirringStirring
  11. customwas continued at 25° C. for 20 additional minutes
  12. temperatureby gentle reflux for 2 hours

Sources & evidence

ORD record
ord-3ff696e2a145474e8c217729347b17b5
Source dataset
uspto-grants-2010_02
Patent number
US07667065B2

Reaction notes

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