Caramelized Pineapple and Jalapeño Margaritas

Instructions

1. In a medium saucepan over medium heat, stir together 1 cup of the sugar and 1 cup water. Heat until the sugar dissolves completely. Remove from heat and add the quartered jalapeño. Let sit for 1 hour. Strain the simple syrup through a fine mesh sieve and store the syrup in the refrigerator until ready to use.
2. In a large pan over medium heat, melt the butter. Add the pineapple over the melted butter and sprinkle with the remaining sugar. Cook the pineapple until caramelized, about 3 minutes per side, basting with the butter-sugar mixture. Remove from heat and let cool completely.
3. Combine the caramelized pineapple, lime juice, 1/4 cup of the simple syrup, tequila, triple sec, and vanilla extract to a blender. Blend until smooth.
4. Pour the mixture into a pitcher and refrigerate until ready to serve.
5. Serve over ice.