Triphenylphosphine → [4-(2-{4-[2-(3-Fluoro-4-methoxy-phenyl)-ethoxy]-phenyl}ethyl)-2-methyl-4,5-dihydro-oxazol-4-yl]-methanol

Participants

Reaction Steps

To a solution of 4-[2-(4-hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol (300 mg, 1.27 mmol) in dry THF (6 ml) is added under inert atmosphere polystyrene supported triphenylphosphine (loading 3 mmol·g−1, 1.27 g, 3.81 mmol, 3 eq.), 2-(3-fluoro-4-methoxyphenyl)-ethanol (647.7 mg, 3.81 mmol, 3 eq.) and DBAD (877.3 mg, 3.81 mmol, 3 eq.). The reaction mixture was stirred under inert atmosphere at room temperature overnight. Polystyrene supported triphenylphosphine was then filtered through frit and washed with ethyl acetate and methanol. The reaction mixture was then concentrated to dryness following by addition of 4M HCl in dioxane (3 ml), the reaction was stirred at room temperature for 3 hours. The reaction mixture was quenched by addition of saturated solution of NaHCO3 (10 ml) and ethyl acetate (40 ml). The organic layer is separated and the aqueous phase is extracted with ethyl acetate (3×40 ml). The combined organic extracts are washed with brine, dried over MgSO4, and evaporated to dryness. Purification using Flashmaster (chexane/ethyl acetate (1/9), ethyl acetate and ethyl acetate/methanol (98/2)) affords [4-(2-{4-[2-(3-fluoro-4-methoxy-phenyl)-ethoxy]-phenyl}ethyl)-2-methyl-4,5-dihydro-oxazol-4-yl]-methanol as colorless oil. MS (ESI+): 364.2 (MH+)

Provenance & Evidence