Triphenylphosphine → HCID 10116916, compound

Participants

Reaction Steps

A solution of triphenylphosphine (1.8 mmol) in 50 mL of dry THF was treated at 0° C. with diethylazodicarboxylate (1.8 mmol) and stirred for 20 min. A solution of 3-[4-(6-Hydroxy-hex-1-ynyl)-phenyl]-2-methoxy-propionic acid ethyl ester (Example 49, Step A) (1.2 mmol) and 4-phenoxyphenol (1.8 mmol) in 10 mL of dry THF was added, and the mixture was stirred at room temperature overnight. The mixture was concentrated under vacuum and purified by silica gel chromatography (silica gel, hexanes/ethyl acetate 10:1 to 3:1). Fractions with Rfs 0.48 and 0.45 (hexanes/ethyl acetate 2:1) corresponding to the coupled compound and starting phenol, respectively, were combined and concentrated. The mixture was dissolved in 5 mL of methanol and was treated with a mixture of 0.712 mg of mercury (II) oxide and 12 ml of 4% sulfuric acid in water. The solution was stirred at 55° C. for 3 hours, cooled to room temperature, diluted with saturated aqueous NaHCO3 (20 mL), and extracted with dichloromethane (4×20 mL). The combined organic layers were washed with brine (20 mL), dried (MgSO4), and concentrated. The residue was dissolved in 6 mL of methanol and 2 mL of 1N NaOH and stirred for 2 hours. The methanol was evaporated under vacuum, and the aqueous solution was diluted with brine (6 mL) and washed with diethyl ether (3×15 mL). The aqueous layer was acidified with 1N HCl (pH 1–2) and extracted with ethyl acetate (3×15 mL). The combined extracts were dried (MgSO4) and concentrated to give the title compound. MS(ES) for C28H30O6[M+H]+: 463.2.

Provenance & Evidence