Diethyl Ether → 1-(prop-2-ynyl)cyclopentanol

Magnesium turnings (350 mg, 14.4 mmol) and HgCl2 (16 mg, 0.059 mmol) were stirred with 20 mL of anhydrous diethyl ether in a 100-mL found bottom flask. Propargyl bromide (80% in xylene, 2.5 mL, 13.2 mmol) was added. The mixture, was stirred for 30 min at room temperature before cyclopentanone (1.0 g, 11.9 mmol) was added in 10 mL tetrahydrofuran. The resulting mixture was refluxed for 2 h, then allowed to cool to room temperature, and quenched with saturated aqueous ammonium chloride (15 mL). The biphasic mixture was extracted with ethyl acetate (50 mL) and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuuo. The residue was purified by flash chromatograph on silica gel (eluting with 10% hexanes in ethyl acetate) to provide the title compound (800 mg, 54%) as a colorless oil.

1. temperatureThe resulting mixture was refluxed for 2 h
2. customquenched with saturated aqueous ammonium chloride (15 mL)
3. extractionThe biphasic mixture was extracted with ethyl acetate (50 mL)
4. washthe organic layer was washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuuo
8. customThe residue was purified by flash chromatograph on silica gel (eluting with 10% hexanes in ethyl acetate)

ORD record

ord-58faec69de014c37aa325ec657906eb6

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076344B2