October 02, 2022, 01:52:48 AM
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Topic: deprotection of benzyl groups in the presence of alkynes  (Read 2845 times)

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Offline rolnor

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Re: deprotection of benzyl groups in the presence of alkynes
« Reply #15 on: February 01, 2020, 11:58:39 AM »
update: since the step this was required was right at the end of a long synthesis and material was precious i made a model substrate to screen conditions. i tested the BCl3/ pentamethyl benzene at -78°C on this and it worked a charm and did not touch the alkynes. so i used it on my real substrate and it seemed  to work well.

Nice!

Offline hollytara

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Re: deprotection of benzyl groups in the presence of alkynes
« Reply #16 on: February 01, 2020, 04:16:22 PM »
Always good to test on a model instead of something precious!

I had a colleague drop a flask containing a solution of a compound ~20 steps in and 2 steps from the end of a long synthesis.  Ouch!  He soaked it up with paper towels, wiped the floor with more solvent soaked towels, extracted and re-chromatographed what he got... saved most of it... ended up published in Nature

Offline wildfyr

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Re: deprotection of benzyl groups in the presence of alkynes
« Reply #17 on: February 01, 2020, 11:39:09 PM »
I've heard that referred to as a bench top extraction, because you're extracting and purifying material you've spilled on your bench.

I've done it.

Offline rolnor

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Re: deprotection of benzyl groups in the presence of alkynes
« Reply #18 on: February 02, 2020, 08:09:50 AM »
I've heard that referred to as a bench top extraction, because you're extracting and purifying material you've spilled on your bench.

I've done it.

#Metoo

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