Whitby group

To a solution of ethyl vinyl ether (0.95 mL, 721 mg, 10 mmol) in THF (8 mL) at –70 °C under Ar is added dropwise tert-butyllithium (4.7 mL of a 1.7 M solution in pentanes, 8 mmol), resulting in a bright yellow suspension. The reaction is allowed to warm, resulting in dissolution of the yellow precipitate, and disappearance of the yellow colour at around 0 °C. The solution is re-cooled to –70 °C and a solution of the 1-iodo-2-phenyl-4-pentene (952 mg, 3.5 mmol) in THF (2 mL) is added. After warming to 0 °C and stirring for between 1 h and 5 h, saturated NH₄Cl solution (10 mL) is added. After dilution with ether (20 mL), the aqueous phase is separated and extracted with ether (3 x 50 mL), and the combined organic phases washed with brine, dried over Na₂SO₄, filtered and concentrated. he crude material was purified by Kugelrohr distillation (110 °C, 0.5 mbar). The product (186 mg, 37%) was found to be the result of elimination of HI from the iodide starting material.