Cyclopentadiene → 2-Hydroxyethyl bicyclo[2.2.1]hept-5-ene-2-carboxylate

HRID 1276020Notes

Reaction equation

HRID 1276020 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[C:6]([O:10][CH2:11][CH2:12][OH:13])(=[O:9])[CH:7]=[CH2:8]>C1COCC1>[CH:2]12[CH2:1][CH:5]([CH:7]([C:6]([O:10][CH2:11][CH2:12][OH:13])=[O:9])[CH2:8]1)[CH:4]=[CH:3]2

Participants

4

Reactant 2

HCID 7612CyclopentadieneHCID 131652-Hydroxyethyl acrylate

Product 1

HCID 120338232-Hydroxyethyl bicyclo[2.2.1]hept-5-ene-2-carboxylateYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclopentadiene (66 g) and 140 g of 2-hydroxyethyl acrylate were dissolved in 500 g of THF solvent. After the reaction at 30° C. for 24 hours, the solvent was removed by rotary evaporator. The residue was distilled under reduced pressure to obtain 148 g of 2-hydroxyethyl 5-norbornene-carboxylate as a mixture of endo and exo (yield: 72%). NMR spectral data of the resulting compound (21) is shown in FIG. 4.

Workup

  1. customAfter the reaction at 30° C. for 24 hours
  2. customthe solvent was removed by rotary evaporator
  3. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-bfb129743d954f2cb98541727c54a778
Source dataset
uspto-grants-2000_12
Patent number
US06165672

Reaction notes

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