C(NC(C)C)(C)C.C([Li])CCC.[C:13]1([CH2:19][C:20]#N)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN(P([N:30]([CH3:32])C)(N(C)C)=O)C.ClC[C:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][CH:36]=1>O1CCCC1>[C:43]1([CH2:20][CH2:19][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[C:32]#[N:30])[C:44]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:40]=[CH:41][CH:42]=1A solution of 1.26 mL (911 mg, 9.00 mmol) of diisopropylamine in 50 mL of THF (tetrahydrofuran) was cooled to −78° C. under nitrogen and 5.6 mL (9.0 mmol) of n-butyllithium, 1.6 M in hexanes, was added via syringe. The mixture was stirred at −78° C. for 1 hour and a solution of 353 mg (3.00 mmol) of α-tolunitrile in 10 mL of THF was added. The solution was stirred at −78° C. for one additional hour and a solution of 1.57 mL (9.00 mmol) of HMPA and 583 mg (3.30 mmol) of 1-chloromethylnaphthalene in 10 mL of THF was added dropwise. After stirring for one additional hour at −78° C., the reaction was quenched with water and extracted with Et2O (diethyl ether) (2×30 mL). The organic layer was washed with aqueous 1 N HCl (30 mL), water (3×30 mL), brine (30 mL) and dried (Na2SO4). The solvent was evaporated to give 735 mg of crude product which was used directly in the next step.
Loading…
