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(One-Pot Wittig)


Example 1

To a solution of the aldehyde (A) (25.0 g, 113.1 mmol) in EtOAc (113 mL) was added PPh3 (41.49 g, 158.4 mmol), sat aq NaHCO3 (226 mL), and ethyl 2-bromoacetate (B) (28.34 g, 169.7 mmol). The reaction mixture was stirred vigorously at RT for 3 h. The mixture was diluted with H2O (150 mL) and EtOAc (300 mL). The org layer was washed with H2O (250 mL), brine (250 mL), dried (Na2SO4), and concentrated. The resulting residue was purified by silica gel column chromatography (40:1 PE/EtOAc) to provide the product as a white solid. [33.25 g, 100%]

[Patent Reference: WO2016011930, page 158, (15.7 MB)]