Benzoxazole → 2-Triethylstannylbenzoxazole

反応式

C([Li])CCC.[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1.[CH2:15]([Sn:17](Br)([CH2:20][CH3:21])[CH2:18][CH3:19])[CH3:16]>CCOCC>[CH2:15]([Sn:17]([CH2:20][CH3:21])([CH2:18][CH3:19])[C:7]1[O:6][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=1)[CH3:16]

参加物

反応条件

温度: -78 °C

実験手順

n-Butyllithium (1.6M, 6.0 mL, 9.57 mmol) was added to a solution of benzoxazole (950 mg, 7.98 mmol) in anhydrous ether (20 mL) stirred at −78° C. under nitrogen. After 10 min, triethylstannyl bromide (2.28 g, 7.98 mmol) was added, then the reaction mixture was allowed to warm to room temperature, and stirred for another 1 h. The mixture was quenched, and washed with 1N sodium hydroxide, dried through MgSO4, and then the solvent was evaporated to give the sub-title compound as a brown oily residue which was used directly without further purification for the next step.