Tetrahydrofuran → t-Butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate

HRID 1276021Notes

Reaction equation

HRID 1276021 reaction equation
[CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1.[C:7]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])C=C.[CH2:16]1COC[CH2:17]1>>[CH:2]12[CH2:17][CH2:16][CH:5]([CH:6]=[CH:1]1)[CH2:4][CH:3]2[C:7]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 116051,3-CyclohexadieneHCID 15458tert-Butyl acrylate

Product 1

HCID 18413667t-Butyl bicyclo[2,2,2]oct-5-ene-2-carboxylateYield 48%

Procedure

Cyclohexadiene (80g) and 154 g of t-butyl acrylate were dissolved in 500 g of THF solvent. After reacting at 50° C. for 24 hours, the solvent was removed by rotary evaporator. The residue was distilled under reduced pressure to obtain 112 g of t-butyl bicyclo[2,2,2]oct -5-ene-2-carboxylate as a mixture of endo and exo (yield: 48%).

Workup

  1. customthe solvent was removed by rotary evaporator
  2. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-1038331efefc459bae1e2cd21ec1f519
Source dataset
uspto-grants-2000_12
Patent number
US06165672

Reaction notes

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