What is the mechanism of this reaction? My proposed mechanism is shown below, would it work?
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2$\begingroup$ Sodium hydride is a non-nucleophilic base. $\endgroup$– ZheCommented Aug 23, 2018 at 23:46
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$\begingroup$ Joe kent: Try forming the alkoxide with NaH first and then transfer the CO2Et group either intra- or intermolecularly. The amide ion that is left is ready for alkylation. Try it and see what you get. $\endgroup$– user55119Commented Aug 24, 2018 at 0:25
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$\begingroup$ Not sure the sodium hydride is intended as,a nucleophile. It could react with the benzoyl bromide. $\endgroup$– Oscar LanziCommented Aug 24, 2018 at 16:03
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1 Answer
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NaH is a strong base but a bad nucleophile. This is one possible mechanism.
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2$\begingroup$ Correct about NaH but I can’t agree with that SN2... $\endgroup$ Commented Aug 25, 2018 at 3:20