What is the mechanism of this reaction? My proposed mechanism is shown below, would it work?
$\begingroup$
$\endgroup$
3
-
2$\begingroup$ Sodium hydride is a non-nucleophilic base. $\endgroup$– ZheAug 23, 2018 at 23:46
-
$\begingroup$ 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. $\endgroup$– user55119Aug 24, 2018 at 0:25
-
$\begingroup$ Not sure the sodium hydride is intended as,a nucleophile. It could react with the benzoyl bromide. $\endgroup$– Oscar LanziAug 24, 2018 at 16:03
Add a comment
|
1 Answer
$\begingroup$
$\endgroup$
1
NaH is a strong base but a bad nucleophile. This is one possible mechanism.
-
2$\begingroup$ Correct about NaH but I can’t agree with that SN2... $\endgroup$ Aug 25, 2018 at 3:20