[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][N:10]([CH3:22])[N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21].CCCCCC>C1COCC1>[CH3:22][N:10]([CH3:9])[NH:11][C:19](=[O:20])[C:18]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:12](=[O:21])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1A solution of phenylmagnesium bromide in THF (11.6 mmol) was slowly added to a solution of phthalimide 16 (10.5 mmol) in THF (110 ml) at −78 ° C. and stirred under argon for 15 minutes. The mixture was then progressively warmed to −30 ° C. for 1 hour. The reaction was quenched with a saturated aqueous solution of NH4Cl (15 ml) and the aqueous layer extracted with Et2O. The combined organic layers were washed with brine (20 ml), dried over MgSO4 and the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel chromatography with (1:2) EtOAc:hexane, to give 80% yield of the desired product.
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