Cyclopentadiene → HCID 86754377, compound

HRID 1584628Notes

Reaction equation

HRID 1584628 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.C([CH:9]1CCC(C)C[C:10]21[O:15][C:14](=O)[CH:13]=[CH:12][C:11]2=[O:17])(C)C>ClCCl>[CH3:9][CH2:10][C:11](=[O:17])[CH2:12][CH2:13][C:14](=[O:15])[CH2:1][CH2:5][CH:4]=[CH:3][CH3:2]

Participants

4

Reactant 2

HCID 7612Cyclopentadiene2×HCID 21225077HCID 21225077, compound2×

Product 1

HCID 86754377HCID 86754377, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In this example, D-A reaction of cyclopentadiene with 7-isopropyl-10-methyloxaspiro(5,5)undec-3-ene-2,5-dione is described. The procedure involves stirring of a mixture of 0.132 g of cyclopentadiene, 0.158 g of 7-isopropyl-10-methyl-oxaspiro(5,5)undec-3-ene-2,5-dione and 0.05 g of sulfated zirconia catalyst doped with scandia prepared according to the procedure similar to that of example 1 above, was stirred in 10 ml of dichloromethane at room temperature for 8 h. The catalyst was filtered off. After evaporation of solvent, the residue was chromatographed over silica gel column by eluting with 5% acetone/petroleum ether to give 0.242 g of spiro{2'-isopropyl-5'methylcyclohexane-1,5,4,oxatricyclo[6.2.1.0.2,7 ]undec-9-ene-3,6 dione} (85% yield).

Workup

  1. customprepared
  2. filtrationThe catalyst was filtered off
  3. customAfter evaporation of solvent
  4. customthe residue was chromatographed over silica gel column
  5. washby eluting with 5% acetone/petroleum ether

Sources & evidence

ORD record
ord-fabaa102e45644678bafbbaf14dce5ec
Source dataset
uspto-grants-1999_08
Patent number
US05932752

Reaction notes

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