Sodium hydride → 2,2-Di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}malonic Acid, Benzyl Methyl Ester

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Reaction Steps

To a solution of benzyl methyl malonate (0.2 g) in DMF (8 mL), was added sequentially NaH (0.08 g, 60% in mineral oil), di(tert-butyl) [[4-(bromomethyl)phenyl](difluoro)methyl]phosphonate (0.83 g), and n-Bu4NI (0.08 g). The reaction mixture was stirred at room temperature for 2.5 h, then quenched with 20 mL of saturated aqueous NH4Cl solution and extracted with 50 mL of 1:1 hexane/EtOAc. The extract was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 2:1 hexane/EtOAc. First eluted was 1-benzyl 3-methyl 2-{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}malonate (0.2 g), followed by the title compound (0.3 g) as an oil.

Provenance & Evidence