Cyclopentadiene → 5,5'-(Hexane-2,5-diylidene)di(cyclopenta-1,3-diene)

HRID 865318Notes

Reaction equation

HRID 865318 reaction equation
CC(=O)CCC(=O)C.[CH:9]1[CH2:13][CH:12]=[CH:11][CH:10]=1.N1CCCC1.CC(OC[C:24]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31](COC(C)=O)=[C:30]2C=1C=C[CH:28]=[CH:29]2)=O>CO>[C:10]1(=[C:34]([CH2:35][CH2:36][C:37](=[C:32]2[CH:28]=[CH:29][CH:30]=[CH:31]2)[CH3:24])[CH3:33])[CH:9]=[CH:13][CH:12]=[CH:11]1

Participants

6

Reactant 4

HCID 7612CyclopentadieneHCID 80352,5-HexanedioneHCID 31268PyrrolidineHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

Product 1

HCID 149519975,5'-(Hexane-2,5-diylidene)di(cyclopenta-1,3-diene)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

In a modified reaction procedure [a], 11.0 g (96.3 mmol) of 2,5-hexanedione and 12.7 g (193 mol) of freshly cracked cyclopentadiene are dissolved in 60 ml of methanol, the solution is cooled to 0° C., and 8.60 g (121 mmol) of pyrrolidine are added. The reaction solution is stirred at 0° C. for 90 minutes, hydrolyzed using 5 ml of glacial acetic aaid and 50 ml of water, and extracted twice with 70 ml of diethyl ether in each case, and the combined organic phases are washed with saturated sodium chloride solution and dried over magnesium sulfate, giving, after removal of the solvent in vacuo, 18.0 g (89%) of the difulvene as an orange-red, oily residue.

Workup

  1. extraction50 ml of water, and extracted twice with 70 ml of diethyl ether in each case
  2. washthe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customgiving
  5. customafter removal of the solvent in vacuo, 18.0 g (89%) of the difulvene as an orange-red, oily residue

Sources & evidence

ORD record
ord-203c0b998baa4f2893956ef3aeca67cd
Source dataset
uspto-grants-1996_10
Patent number
US05565534

Reaction notes

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