Hydrochloric Acid → 1-Cyclopentyl-2-phenylethan-1-one

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To a solution of titanium(IV) isopropoxide (5.13 mmol, 1.46 g) in anhydrous tetrahydro-furan (10 mL) was added a solution of cyclopentylmagnesium chloride in THF (7.69 mmol) at −78° C. Reaction was warmed to −50° C. in 5 min, then maintained at that temperature for 8 min and reaction became dark-brown to black. After cooling back to −78° C., 2-phenylacetonitrile (600 mg, 5.13 mmol) was added by a syringe, and the mixture was stirred at −78° C. for 2 h. 1 N HCl aqueous solution was added to quench the reaction. The mixture was extracted with acetic acid ethyl ester (40 mL) for three times, the combined organic layer was washed with brine (30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography to give Intermediate 91 (320 mg, yield: 66.5%) as light green oil.

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