烯基醚的合成基本上可以参考烯烃和醚这两种官能团的合成方法。

羰基化合物与其烯醇式是互变异构体，使用合适的基团使得烯醇式的羟基醚化，即可制得烯基醚化合物。

实例一

To a mixture of S6 (140 mg, 0.285mmol) and tert-butyldimethylsilyl chloride (TBSCl, 86.0 mg, 0.570 mmol)in THF (5.7 mL) was added dropwise potassium bis(trimethylsilyl)amide (KHMDS,0.5 M solution in toluene, 2.0 mL) at –78 °C, and the resulting mixture was stirred for 3 h. The reaction was quenched with saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Purification of the residue by flash column chromatography using diol silica gel (DIOL MB 100-40/75) with ethyl acetate/n-hexane(1:4) afforded 6 (148 mg, 86%) as a colorless oil.

Reference: Org. Lett. 2014, 16, 768-771.

实例二

In a 50 mL round bottomed flask methyl acetoacetonate (20.0 g,172 mmol, 1.0 eq), trimethylorthoformate (18.6 g, 175 mmol, 1.0 eq) and concentrated H₂SO₄ (6 drops) were added and stirred at 20°C for 24 h. After this time, a slight excess of quinoline (12 drops) was added to neutralize the acid. Distillation under reduced pressure afforded the(E)-methyl-3- methoxybut-2-enoate 15a. Colourless liquid, yield (19.5 g, 149mmol,87% yield).

Reference: J.Am.Chem.Soc. 2012, 134, 19362-19365

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