In this study aluminum isopropyl oxide ($Al(O-i-Pr)_3$) was supported on the amine-functionalized surface of silica to synthesize high molecular weight (MW) polylactide (PLA), and it was tested for PLA polymerization behaviors. A silica was funtionalized with silane compound having amine groups, then in-situ treated with $Al(O-i-Pr)_3$. $Al(O-i-Pr)_3$ attached to amine group on silica showed activity only in the presence of MAO (methyl aluminoxane). At the polymerization temperature of $115^{circ}C$, the conversion and the MW of PLA were increased as the amount of silane was increased. At the polymerization temperature of $130^{circ}C$, the conversion was decreased while the MW was increased drastically and reached to MW 44000 g/mol when the amine concentration was 3.0 mmol/g. A bimodal type GPC curve was shown at the polymerization temperature of $115^{circ}C$. As the amount of amine group increased, the peaks of GPC curve were merged. At the polymerization of $130^{circ}C$, a unimodal GPC curve was shown. $Al(O-i-Pr)_3$ supported on amine-functionalized silica was able to produce higher MW PLA with enhanced activity compared to homogeneous $Al(O-i-Pr)_3$.