Ethyl Acetate → (E)-1-Bromo-8-(but-3-enyloxy)cyclooct-1-ene

HRID 1037695Notes

Reaction equation

HRID 1037695 reaction equation
Br[C:2]1([Br:10])[CH:9]2[CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2.[CH2:11]([OH:15])[CH2:12][CH:13]=[CH2:14].CCOC(C)=O>C1(C)C=CC=CC=1.[Al]>[Br:10][C:2]1=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[O:15][CH2:11][CH2:12][CH:13]=[CH2:14]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 693893-Buten-1-olHCID 127597888,8-Dibromobicyclo[5.1.0]octane

Product 1

HCID 66672529(E)-1-Bromo-8-(but-3-enyloxy)cyclooct-1-ene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 5359268AluminumSolvent

Procedure

The compound 1 (2.73 g, 10.18 mmol) and 3-buten-1-ol (8.75 ml, 100.7 mmol, 10 eq.) are placed in anhydrous toluene (50 ml) in a round-bottomed flask wrapped in aluminum. AgClO4 (6.33 g, 30.53 mmol, 3 eq.) is added and the suspension is stirred at ambient temperature for 48 h. After addition of 150 ml of AcOEt and filtering, the solution is washed with deionized water. The organic phase recovered is dried over MgSO4, filtered and purified by flash chromatography (cyclohexane/AcOEt 99:1). The product 2 obtained (1.45 g, 5.59 mmol, 55%) is in the form of a yellow oil.

Workup

  1. filtrationfiltering
  2. washthe solution is washed with deionized water
  3. customThe organic phase recovered
  4. dry with materialis dried over MgSO4
  5. filtrationfiltered
  6. custompurified by flash chromatography (cyclohexane/AcOEt 99:1)

Sources & evidence

ORD record
ord-41051b8073c14f078e4ef47593e37d0c
Source dataset
uspto-grants-2013_10
Patent number
US08546598B2

Reaction notes

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