Doing some preliminary research on the synthesis of 2C-E; UTFSE yielded Shulgin's synth,
Post 41646 (missing)
(psyloxy: "Re: 2,5-Dimethoxybenzaldehyde Hey, OS, Bekr, Mistr", Chemistry Discourse),
Post 60192 (missing)
(yellium: "Another route to 2C-[BDE]", Chemistry Discourse),
Post 263890
(poix: "alkylation of quinones", Novel Discourse),
Post 404204 (missing)
(psygn: "2C-H ---> 2C-E", Chemistry Discourse).
So if I understand Shulgin's synth, he starts with p-dimethoxy benzene, puts a methyl ketone in what becomes the 4 position, and then turns that into an ethyl (in a reaction that sounds messy and has a poor yield).
Then he puts an aldehyde in the 1 position, converts the molecule into the beta nitrostyrene with nitromethane and ammonium acetate, and reduces that with LAH to get 2C-E.
It strikes me that Shulgin first puts the ethyl group in, and only then makes the aldehyde. Can one start with 2,5 dimethoxybenzaldehyde and then put an ethyl group in the 4 position (without protecting the aldehyde group)?
From a couple of the abovementioned posts, it seems like BuLi is a reagent that allows selective alkylation with alkyl halides. Could it be of use ethylating the dimethoxybenzaldehyde at only the 4 position?
If not, how could it be used with 2C-H to get 2C-E. Would one have to go through 2C-B first?
Sorry if my questions are naive; I am just starting to learn organic chemistry, all comments welcome.
