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

HRID 393497Notes

Reaction equation

HRID 393497 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[OH:6][CH2:7][CH2:8][O:9][C:10](=[O:13])C=C.O1CC[CH2:16][CH2:15]1>CCOCC>[CH:2]12[CH2:1][CH:5]([CH:15]=[CH:16]1)[CH2:4][CH:3]2[C:10]([O:9][CH2:8][CH2:7][OH:6])=[O:13]

Participants

5

Reactant 3

HCID 7612CyclopentadieneHCID 8028TetrahydrofuranHCID 131652-Hydroxyethyl acrylate

Product 1

HCID 120338232-Hydroxyethyl bicyclo[2.2.1]hept-5-ene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Cyclopentadiene of Formula VI and 2-hydroxyethylacrylate of the following Formula VII are dissolved at the same rate in ether or tetrahydrofuran and reacted at a temperature of about −30 to 60° C. for 24 hours. Thereafter, the solvent is removed by use of a rotary evaporator and the residue is distilled in vacuo to give 2-hydroxyethyl 5-norbornene-2-carboxylate of the following Formula VIII, which occurs in an endo- and exo-mixture.

Workup

  1. customThereafter, the solvent is removed by use of a rotary evaporator
  2. distillationthe residue is distilled in vacuo

Sources & evidence

ORD record
ord-9339253a88734e3f892f69798456d9dd
Source dataset
uspto-grants-2004_10
Patent number
US06808859B1

Reaction notes

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