Triphenylphosphine → 2,3-Difluoro-6-nitro{[2-(tetrahydropyran-2-yl)oxypropyl]oxy}benzene

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Reaction Steps

To a solution of 2.04 g of triphenylphosphine in 10 ml of anhydrous tetrahydrofuran was added dropwise 1.36 g of diethyl azodicarboxylate with stirring under cooling with ice, and the resulting mixture was stirred at the same temperature for 30 minutes. To this solution was added dropwise a solution of 1.05 g of 2,3-difluoro-6- nitrophenol (IV, Xa=Xb=F), 1.01 g of 2-O-(tetra-hydropyran-2-yl)propane-1,2-diol (III, Rc=THP) in 5 ml of anhydrous tetrahydrofuran and then the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and to the residue was added benzene and a saturated sodium bicarbonate aqueous solution. After the mixture was shaken, the organic layer was separated and washed successively with water and a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The residue was purified through silica gel column to yield 1.85 g of the titled compound.

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