Tetrahydrofuran → Methyl 3-[(e)-1-{4-[[di(tert-butoxy)phosphoryl](difluoro)methyl]benzyl}-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoate

Participants

Reaction Steps

To a degassed solution of the product from Step 2 (0.30 g, 0.77 mmol), 18-Crown-6 (102 mg, 0.39 mmol), and Bu4NI (28 mg, 0.077 mmol) in THF at −78° C. was added the KOtBu solution. After 15 min. at −78° C., a solution of di(tert-butyl)(4-(bromomethyl)phenyl)(difluoro)methyl phosphonate (Example 1, Step 7) (319 mg, 0.77 mmol) in THF (3 mL) via double-tipped needle. The cold bath was removed and the reaction was stirred at r.t. for 1.5 h. Saturated NH4Cl solution was then added and the product was extracted with EtOAc. The organic layer was washed with H2O and brine, and was then dried (MgSO4), filtered, and evaporated. The residue was purified by flash chromatography (1:20 Et2O: toluene, 1% Et3N) to give an oil (98 mg).

Provenance & Evidence