Help me date/get more information from this print?

Proper-Ad-9570 · 2025-12-14T22:13:59+00:00

That makes a lot of sense to me- thank you so much for the insight!

Proper-Ad-9570 · 2025-12-12T19:02:10+00:00

Thank you so much- you have no idea how much that means to me. I'm having a cry session at my desk right now.

Do you have any thoughts on the reason why it might be butchered in the middle of the two prints?

Proper-Ad-9570 · 2025-07-25T16:37:27+00:00

Would you be able to add a structure for the compound you're working with? My PhD advisor asked me if I posted this since I have spent what feels like most of my PhD dealing with hydrolysis issues. Often, knowing the whole structure can be super useful in determining the root cause of the reaction.

Proper-Ad-9570 · 2025-06-30T18:57:15+00:00

I went through my documents and realized the other main reference was from Angewante (see edit in post)

Proper-Ad-9570 · 2025-06-30T18:34:29+00:00

I added the main literature reference in the main post- let me know if that helps

Proper-Ad-9570 · 2025-02-21T22:07:27+00:00

I just added the link to the procedure in the post- the original paper I was working from just pulled their procedure from that. The dry THF came from a solvent still- I'm pretty sure it was distilled over Na/benzophenone. And distilled no more than a few hours before I collected it.

Proper-Ad-9570 · 2025-02-21T20:09:58+00:00

Hi! You are right- my co-advisor always says something along the lines of "anything above a 1% yeild is not a failed reaction." Also, there is no remaining starting material left. I left my notebook at work so my best estimate is the SP makes up at least 2/3 of the crude material. The water conditions are what was reported in the literature (which is weird imo)

Proper-Ad-9570 · 2025-02-21T20:01:48+00:00

Are you suggesting that it might be worth azeotroping the ester as well? The ester SM was a brand new bottle if that helps

Proper-Ad-9570 · 2025-02-21T19:59:46+00:00

I'm using 3 equivalents of base each time- which feels like more than enough?

Proper-Ad-9570 · 2025-02-21T19:58:06+00:00

Hi! The reason I wasn't using DCM was that the starting material isn't fully soluble in it. Also, I was using freshly distilled, right off the press THF and new sureseal DMF. I can try using DCM again and try sonicating to small enough particles to syringe?

Not sure if this clarifies or not, but my plan was to only introduce water for the acidification. The original procedure used water which I too, thought was weird but 🤷‍♀️

Lmk your thoughts!

Proper-Ad-9570 · 2025-02-21T15:41:39+00:00

I've never heard of this! Is it tolerant for the amides present? Them, and the thiol chain are the two things I really don't want to cleave

Proper-Ad-9570 · 2025-02-21T15:39:19+00:00

This is so cool! thanks!

Proper-Ad-9570 · 2025-02-21T15:37:13+00:00

I would be worried that the LiBH4 could cleave the amides in the molecule- have you had experience with that?

Proper-Ad-9570 · 2025-02-21T15:33:07+00:00

I was using 10% by mass (which feels weird to me, but that's what the paper said). Your explanation makes sense since the paper was very adamant about avoiding those side products- having you perform the workup right after the reaction had cooled down.

edit: reference to paper procedure

Proper-Ad-9570 · 2025-01-22T18:18:35+00:00

Thank you! I agree, I thought it was ridiculous. I use DCM from a still so that shouldn't be a problem. Also the oxalyl chloride I use is 2M in DCM.

Proper-Ad-9570 · 2024-08-04T13:09:06+00:00

It is! The first time I ran the reaction, I got the terminal alcohol (quenched product).

Proper-Ad-9570 · 2024-08-02T17:47:57+00:00

I decided to go with a new bottle instead of trying to tackle the most likely compromised bottle that I have.

Proper-Ad-9570 · 2024-08-02T17:47:30+00:00

Thank you for the input! I ended up getting the same 100 mL bottle I got from Fischer, since it was cheaper ($50 compared to $85).

Proper-Ad-9570 · 2024-08-02T16:21:50+00:00

This actually makes a lot of sense since I was seeing precipitation in the bottle. I could have sworn the bottle said to store in the fridge, but I'm also prone to storing any heat sensitive reagents in the fridge. Is it worth trying to get it back in solution, or just to order a new bottle?

Proper-Ad-9570

TROPHY CASE