Isopropyl iodide → 2,2-dimethyl-8-(propan-2-yloxy)-4H-1,3-benzodioxin-4-one

反応式

C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[C:13]2[O:14][C:15]([CH3:20])([CH3:19])[O:16][C:17](=[O:18])[C:12]=2[CH:11]=[CH:10][CH:9]=1.I[CH:22]([CH3:24])[CH3:23]>CN(C)C=O>[CH3:19][C:15]1([CH3:20])[O:14][C:13]2[C:8]([O:7][CH:22]([CH3:24])[CH3:23])=[CH:9][CH:10]=[CH:11][C:12]=2[C:17](=[O:18])[O:16]1

参加物

実験手順

Cesium carbonate (5.46 g, 16.6 mmol) was added to a solution of 8-hydroxy-2,2-dimethyl-4H-1,3-benzodioxin-4-one (123a, 1.50 g, 7.73 mmol) in N,N-dimethylformamide (31 mL) and the mixture stirred at room temperature for five minutes before 2-iodopropane (1.00 mL, 10.0 mmol) was added. The mixture was stirred at room temperature for 80 minutes, then partitioned between deionized water (30 mL) and ethyl acetate (2×75 mL). The combined organic extracts were dried over magnesium sulfate, filtered, concentrated under vacuum, and purified by column chromatography (ethyl acetate/heptane) to give 2,2-dimethyl-8-(propan-2-yloxy)-4H-1,3-benzodioxin-4-one (123b, 1.41 g, 77% yield) as a colorless gel which slowly crystallized to a white solid.