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[Wittig Reagent (stable)]


Example 1

A mixture of the SM (1.0 g, 3.11 mmol) and (carbethoxymethylene)triphenylphosphorane (2.11 g, 6.22 mmol) in toluene (30 mL) was refluxed for 16 h. The solvent was removed in vacuo and the resulting residue was purified by silica gel column chromatography to provide the product as a white solid. [1.05 g, 84%]

[Patent Reference: WO2015088045, page 163, (10.3 MB)]

Example 2

(Carbethoxymethylene)triphenylphosphorane (12 g, 34 mmol) was added in one portion to a mixture of the SM (2.3 g, 22 mmol) in dry DCM (144 mL). The reaction mixture was stirred at RT overnight. The mixture was concentrated and purified by Prep silica LC (10-20% EtOAc/heptane) to provide the product as a colorless oil. [0.82 g, 21%]

[Patent Reference: WO2016020526, page 65, (5.6 MB)]