Lithium Chloride → 2-(Trimethylsilyl)ethyl 2-(2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxo-propyl)phenyl)butanoate

Participants

Reaction Conditions

Reaction Steps

To a mixture of LiCl (3.26 g, 77 mmol), LiOAc (19.6 g, 192 mmol), n-Bu4NCl (42.7 g, 154 mmol), Pd (OAc)2 (0.52 g, 2.3 mmol) and the allyl alcohol of Example 80, Step 1 (24.7 g, 77 mmol) under N2 was added a solution of the aryl iodide of Step 2 (30.0 g, 77 mmol) in DMF (150 mL). The suspension was degassed and purged with N2, and was then stirred at 100° C. for 1 h. The dark red solution was then poured onto a mixture of ice (300 g) and saturated NaHCO3 (300 mL). The red syrup was extracted with EtOAc. Following filtration through celite, the organic phase was washed with H2O and saturated NaCl solution. After drying (MgSO4), the solvent was removed under vacuum and the residue was purified by flash chromatography. Elution was effected with 1:20 EtOAc:hexane, followed by 1:10 EtOAc:hexane to give 37.4 g of the title compound as a white solid, mp 109°-111° C.

Provenance & Evidence