Boron trifluoride etherate → HCID 21072805, compound

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Reaction Steps

A suspension of 6.0 g (26 mmol) of 3-(4,4-dimethyl-2-oxo-4H-benzo[d][1,3]oxazin-1-yl]propionitrile in 120 mL of diethyl ether is combined with 16.5 mL (56 mmol) of titanium tetraisopropoxide while being cooled with an ice bath. Then 18.5 mL of a 3 molar solution of ethylmagnesium bromide in diethyl ether is added dropwise such that the temperature does not climb past 20° C. The mixture is stirred for 30 minutes at ambient temperature and 7.0 mL (55 mmol) boron trifluoride-diethyl ether is added batchwise while cooling with an ice bath. The mixture is stirred for one hour at ambient temperature and 150 mL of a 1 molar sodium hydroxide solution is added dropwise while cooling. The reaction mixture is diluted with diethyl ether and the phases are separated. The aqueous phase is extracted with diethyl ether and the combined organic phases are extracted with sodium sulfite solution and repeatedly extracted with 1 molar hydrochloric acid. The hydrochloric acid phases are combined, extracted with diethyl ether, made alkaline with sodium hydroxide solution, and exhaustively extracted with dichloromethane. The dichloromethane phases are dried with sodium sulfate and evaporated down. Light yellow oil. Yield: 1.5 g (22%); mass spectroscopy: [M+H]+=261.

Provenance & Evidence