3-Tert-butyl-2,2-dichlorocyclobutanone → 3-Tert-butylcyclobutan-1-one

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Reaction Steps

Saturate dry methanol by stirring with excess ammonium chloride under nitrogen for 1.5 h. Add this saturated solution (150 mL) to 3-tert-butyl-2,2-dichlorocyclobutanone (7.5 g, 38.4 mmol) under nitrogen. To the resulting suspension add freshly activated zinc (15.4 g, 236 mmol). Stir for 5 hours, filter and concentrate. Partition the residue between diethyl ether and water. Discard the aqueous phase and wash the diethyl ether layer with water (twice), saturated aqueous sodium chloride solution, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes) to give the desired compound as a clear liquid (2.71 g, 56%).

Provenance & Evidence