Chlorotrimethylsilane → 3-(Propan-2-yl)cyclopentan-1-one

Temperature

-70 °C

To a solution of cyclopent-2-enone (1.5 mL, 18.27 mmol), CuBr—SMe2 (188 mg, 0.91 mmol), chlorotrimethylsilane (4.59 mL, 36.54 mmol) amd HMPA (6.55 g, 36.54 mmol) in THF (30 mL) was added isopropylmagnesium bromide (36.54 mL, 1 M in THF) at −70° C. After stirring for 1 h at −70° C., the reaction mixture was quenched with HCl (10%). The mixture was extracted with Et2O. The organic layer was washed with aqueous NaHCO3 and brine. After dried over Na2SO4, the organic layer was concentrated to give 3-isopropylcyclopentanone (4 g, 100%).

1. customthe reaction mixture was quenched with HCl (10%)
2. extractionThe mixture was extracted with Et2O
3. washThe organic layer was washed with aqueous NaHCO3 and brine
4. dry with materialAfter dried over Na2SO4
5. concentrationthe organic layer was concentrated

ORD record

ord-10268c329fcc45028269a2d8389e8533

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450308B2