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

HRID 1276018Notes

Reaction equation

HRID 1276018 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.[CH2:15]1COC[CH2:16]1>>[CH:2]12[CH2:1][CH:5]([CH:15]=[CH:16]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 77.3%

Procedure

Cyclopentadiene (66 g) and 154 g of t-butyl acrylate were dissolved in 500 g of THF solvent. After the reaction at 30° C. for 24 hours, the solvent and excess t-butyl acrylate were removed in rotary evaporator. The residue was distilled under reduced pressure to obtain 150 g of t-butyl 5-norbornene- 2-carboxylate as a mixture of endo and exo (yield: 68%). NMR spectral data of the resulting compound (19) is shown in FIG. 2.

Workup

  1. customAfter the reaction at 30° C. for 24 hours
  2. customthe solvent and excess t-butyl acrylate were removed in rotary evaporator
  3. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-40893967f10943a891d702999a527b09
Source dataset
uspto-grants-2000_12
Patent number
US06165672

Reaction notes

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