Methyl 2-(2-isopropyl-1,3-dioxolan-2-yl)acetate → 2-[2-(Propan-2-yl)-1,3-dioxolan-2-yl]ethan-1-ol

Participants

Reaction Conditions

Reaction Steps

In a flame-dried, three-neck flask equipped with an addition funnel, magnetic stirring bar, rubber septum, and a nitrogen inlet, was placed LiAlH4 (3.12 g, 82.1 mmol) and tetrahydrofuran (700 mL). After being cooled at 0° C., a solution of (2-isopropyl-[1,3]dioxolan-2-yl)-acetic acid methyl ester (12 g, 63.8 mmol) in tetrahydrofuran (160 mL) was added dropwise with stirring. The mixture was warmed to room temperature and stirred for 24 hours. The reaction was quenched by adding water (5 mL), 15% aqueous NaOH (10 mL), and water (5 mL) slowly. The organic layer was separated, and the residue was extracted with EtOAc (3×100 mL). The combined organic phase was dried over Na2SO4 and concentrated to afford the crude product, which was purified by column chromatography to give 2-(2-isopropyl-[1,3]dioxolan-2-yl)-ethanol (6.8 g, 67%). 1H NMR (CDCl3) δ 0.90 (d, J=6.8 Hz, 6H), 1.87-1.96 (m, 3H), 2.81 (br, 1H), 3.69-3.72 (m, 2H), 3.92-4.01 (m, 4H).

Provenance & Evidence