The Synthesis of The Hetero-Oxazole - Haverford College Superlab Q2

[AronSchwartzHC]

Jessica Koshinski and I will be taking over "The Synthesis of the Heterooxazole" in Quarter 2 Superlab at Haverford College. We will be recording our work in this lab notebook: "http://malaria.ourexperiment.org/synthesis_of_hetero".

Below is the most recent proposed scheme:

[mattodd]

Hi @AronSchwartzHC - as per previous issue could you please take a look at these guidelines and include them in what you're doing?

However, in this case, are you talking about an oxazole, or an oxadiazole ring? If you could please alter the title of this Issue to reflect that, and try to keep the terminology consistent? Remember that you have to write up your work so that others, unfamiliar with what you're doing, can understand it and navigate around your project without necessarily having to come back to you for clarification - this will ultimately help you!

[MFernflower]

@mattodd looks like there making an oxazole

[mattodd]

Cross-reference to synthetic ideas for the oxadiazole in #448 and #463 re @JohnATucker's suggestion of Pd-catalysed couplings to install hetero ring - see above scheme.

@AronSchwartzHC your original post also said you were going to look at the 6 and the 8, which I assume is a type and I've corrected it. You also say you're "taking over" the synthesis of the oxazole. I don't have any record of previous work towards this target. Have we missed something? (check out the DCNYS wiki section).

However, a big request for the way @AronSchwartzHC and Jessica are using the ELN here - please include chemical schemes (so humans can read the lab book) and logical compound numbering (so we can navigate what you're doing) and SMILES/InChI/InChIKey strings (so Google knows what you're doing). At the moment the ELN is hard to understand. @rbroadrup-HC

[AronSchwartzHC]

@mattodd, I changed the name to just "The Synthesis of The Hetero-Oxazole - Haverford College Superlab Q2" since there wasn't a previous group that was working on this compound. We are now working to change the appearance of our ELN.

[MFernflower]

It would be nice to show the route to that phenyloxazole compoud as article is paywalled @mattodd @AronSchwartzHC

[AronSchwartzHC]

I apologize for never getting back to you @MFernflower. Here is the route that I followed:

I completed this synthesis about 3 weeks ago and only got ~10% yield. I redid the synthesis this week (to maximize yield) and will check to see how much product I was able to synthesize. The literature reports a 66% yield at best.

[MFernflower]

I'd bet a good amount of the product was lost during purification.

[AronSchwartzHC]

I was able to synthesis 2-phenyloxazole in about 25% yield.

Has anyone had any success on a similar compound using this coupling reaction on these OSM series 4 cores?

The paper that I'm referencing used iodobenzene to couple penyloxazoles and reported that coupling with pyridyl iodides resulted in lower yields (30-36%). This mades me skeptical about my reaction. I have limited amounts of 2-phenyloxazole and I wanted to hear if anyone had any recommendations.

Here is the supplement section in which I have referenced for the above reaction:
http://www.rsc.org/suppdata/cc/b7/b719466h/b719466h.pdf

[MFernflower]

That is a question for @edwintse

BTW my real name is Anthony. I feel silly when people call me by my old minecraft username when talking about chemistry