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

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Reaction Steps

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.

Provenance & Evidence