Cyclopentadiene → Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl ester

HRID 393498Notes

Reaction equation

HRID 393498 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[C:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])C=C.O1CC[CH2:17][CH2:16]1>>[CH:2]12[CH2:1][CH:5]([CH:16]=[CH:17]1)[CH2:4][CH:3]2[C:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

4

Reactant 3

HCID 7612CyclopentadieneHCID 8028TetrahydrofuranHCID 15458tert-Butyl acrylate

Product 1

HCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl esterYield 90%

Procedure

66 g of cyclopentadiene is first put in a reactor and then mixed with 500 g of tetrahydrofuran. 128 g of t-butyl acrylate is added to the reactor. Thereafter, these reactants are subjected to a reaction at a temperature of −30 to 60° C. for 10 hrs with stirring. After the completion of the reaction, the solvent is vaporized in vacuo by use of a rotary evaporator, then vacuum distilled to produce the subject compound: yield is 90%.

Workup

  1. customThereafter, these reactants are subjected to a reaction at a temperature of −30 to 60° C. for 10 hrs
  2. customAfter the completion of the reaction
  3. customthe solvent is vaporized in vacuo by use of a rotary evaporator
  4. distillationvacuum distilled
  5. customto produce the subject compound

Sources & evidence

ORD record
ord-49640d95e0ba48a3a98239e0763c1205
Source dataset
uspto-grants-2004_10
Patent number
US06808859B1

Reaction notes

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