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

Temperature

0 °C

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).

1. customIn a flame-dried, three-neck flask equipped with an addition funnel, magnetic stirring bar
2. temperatureThe mixture was warmed to room temperature
3. stirringstirred for 24 hours
4. customThe reaction was quenched
5. additionby adding water (5 mL), 15% aqueous NaOH (10 mL), and water (5 mL) slowly
6. customThe organic layer was separated
7. extractionthe residue was extracted with EtOAc (3×100 mL)
8. dry with materialThe combined organic phase was dried over Na2SO4
9. concentrationconcentrated
10. customto afford the crude product, which
11. customwas purified by column chromatography

ORD record

ord-08c7afd4a9024b5d8ec6cacaff0ec439

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846668B2