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 THF (700 mL). After being cooled at 0° C., a solution of methyl 2-(2-isopropyl-1,3-dioxolan-2-yl)acetate (12 g, 63.8 mmol) in THF (160 mL) was added dropwise with stirring. The mixture was warmed to rt, 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
2. customequipped with an addition funnel, magnetic stirring bar
3. temperatureThe mixture was warmed to rt
4. stirringstirred for 24 hours
5. customThe reaction was quenched
6. additionby adding water (5 mL), 15% aqueous NaOH (10 mL), and water (5 mL) slowly
7. customThe organic layer was separated
8. extractionthe residue was extracted with EtOAc (3×100 mL)
9. dry with materialThe combined organic phase was dried over Na2SO4
10. concentrationconcentrated
11. customto afford the crude product, which
12. customwas purified by column chromatography

ORD record

ord-b3502f6f50b14fd5a2ab0a674d779534

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08754076B2