Iodoethane → HCID 10036828, compound

To a freshly prepared solution of lithium diisopropylamide (40.0 mmol in tetrahydrofuran/hexane; 50 mL, 1:1) at −78° C. was added a solution of ethyl-4-(2-methyl-1,3-dioxolan-2-yl)butanoate (6.7 g, 33.3 mmol) in tetrahydrofuran (15 mL) over 15 minutes. After stirring for 15 minutes, ethyl iodide (4.0 mL, 50.0 mmol) was added rapidly via syringe. The reaction was stirred at −78° C. for 6 hours and then allowed to warm slowly to ambient temperature and stir for 16 hours. The reaction was quenched by the addition of water (50 mL) and extracted with ether (3×50 mL). The combined organics were washed with brine (50 mL), dried (magnesium sulfate), concentrated in vacuo and chromatographed (silica gel, ethyl acetate/hexane, 1:4) to afford ethyl 2-ethyl-4-(2-methyl-1,3-dioxolan-2-yl)butanoate (2.6 g, 33%) as a colorless liquid.

1. stirringThe reaction was stirred at −78° C. for 6 hours
2. stirringstir for 16 hours
3. customThe reaction was quenched by the addition of water (50 mL)
4. extractionextracted with ether (3×50 mL)
5. washThe combined organics were washed with brine (50 mL)
6. dry with materialdried (magnesium sulfate)
7. concentrationconcentrated in vacuo
8. customchromatographed (silica gel, ethyl acetate/hexane, 1:4)

ORD record

ord-484ba7ebdfb343dd99a7b8afe20e6879

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06617350B2