New issue

Have a question about this project? Sign up for a free GitHub account to open an issue and contact its maintainers and the community.

By clicking “Sign up for GitHub”, you agree to our terms of service and privacy statement. We’ll occasionally send you account related emails.

Already on GitHub? Sign in to your account

The Synthesis of The Hetero-Oxazole - Haverford College Superlab Q2 #462

Open
AronSchwartzHC opened this Issue Nov 5, 2016 · 9 comments

Comments

Projects
None yet
3 participants
@AronSchwartzHC

AronSchwartzHC commented Nov 5, 2016

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:
image

@mattodd

This comment has been minimized.

Show comment
Hide comment
@mattodd

mattodd Nov 8, 2016

Member

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!

Member

mattodd commented Nov 8, 2016

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!

@AronSchwartzHC AronSchwartzHC changed the title from Taking Over Synthesis of "The Hetro-Oxide" - Haverford College Superlab Q2 to Taking Over Synthesis of "The Hetro-Oxazole" - Haverford College Superlab Q2 Nov 9, 2016

@MFernflower

This comment has been minimized.

Show comment
Hide comment
@MFernflower

MFernflower Nov 16, 2016

Contributor

@mattodd looks like there making an oxazole

Contributor

MFernflower commented Nov 16, 2016

@mattodd looks like there making an oxazole

@mattodd mattodd changed the title from Taking Over Synthesis of "The Hetro-Oxazole" - Haverford College Superlab Q2 to Taking Over Synthesis of "The Hetero-Oxazole" - Haverford College Superlab Q2 Nov 16, 2016

@mattodd

This comment has been minimized.

Show comment
Hide comment
@mattodd

mattodd Nov 16, 2016

Member

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

Member

mattodd commented Nov 16, 2016

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

This comment has been minimized.

Show comment
Hide comment
@AronSchwartzHC

AronSchwartzHC Nov 16, 2016

@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.

AronSchwartzHC commented Nov 16, 2016

@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.

@AronSchwartzHC AronSchwartzHC changed the title from Taking Over Synthesis of "The Hetero-Oxazole" - Haverford College Superlab Q2 to The Synthesis of The Hetero-Oxazole Nov 16, 2016

@AronSchwartzHC AronSchwartzHC changed the title from The Synthesis of The Hetero-Oxazole to The Synthesis of The Hetero-Oxazole - Haverford College Superlab Q2 Nov 16, 2016

@MFernflower

This comment has been minimized.

Show comment
Hide comment
@MFernflower

MFernflower Jan 21, 2017

Contributor

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

Contributor

MFernflower commented Jan 21, 2017

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

@AronSchwartzHC

This comment has been minimized.

Show comment
Hide comment
@AronSchwartzHC

AronSchwartzHC Jun 22, 2017

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

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.

AronSchwartzHC commented Jun 22, 2017

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

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

This comment has been minimized.

Show comment
Hide comment
@MFernflower

MFernflower Jun 22, 2017

Contributor

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

Contributor

MFernflower commented Jun 22, 2017

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

@AronSchwartzHC

This comment has been minimized.

Show comment
Hide comment
@AronSchwartzHC

AronSchwartzHC Jun 26, 2017

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?
image

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

AronSchwartzHC commented Jun 26, 2017

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?
image

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

This comment has been minimized.

Show comment
Hide comment
@MFernflower

MFernflower Jun 26, 2017

Contributor

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

Contributor

MFernflower commented Jun 26, 2017

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

Sign up for free to join this conversation on GitHub. Already have an account? Sign in to comment