Isopropanol → 1-(2-Chloro-1-cyclopentenyl)ethanol

Under an argon atmosphere, 2-chloro-1-cyclopentenecarbaldehyde (630 mg, 4.82 mmol) was dissolved in anhydrous tetrahydrofuran (19 ml), methylmagnesium bromide (1.4M toluene solution, 4.1 ml) was added dropwise at 0° C., and the mixture was stirred at room temperature for 30 minutes. Isopropanol (2 ml) was added at 0° C., and the solvent was evaporated under reduced pressure. 1N Hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1-6:1) to give the title compound (294 mg, 2.01 mmol, 41.6%).

1. customthe solvent was evaporated under reduced pressure
2. addition1N Hydrochloric acid was added
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with saturated aqueous sodium chloride solution
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1-6:1)

ORD record

ord-6b7a704ec95a4182aae2e8c3e4be803a

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517996B2