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Topic: diethylamino trimethylsilane (DEATMS)  (Read 3557 times)

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Offline AlphaScent

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diethylamino trimethylsilane (DEATMS)
« on: June 02, 2014, 02:35:18 PM »
This is a base that is used in a reaction procedure I am trying.  It is used in the Michael reaction step of a Robinson annulation. 

The paper mentions that diethylamine can be used.  Does not say how well it works, however. 

If one had chlorotrimethylsilane and diethyl amine; couldnt you just make it?

I would say in a polar aprotic solvent such as ether.  Add the nucleophile to the electrophile at 0 degrees.

What do you think?

Google was not much help for the synthesis of diethylamino trimethylsilane
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Offline discodermolide

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Re: diethylamino trimethylsilane (DEATMS)
« Reply #1 on: June 02, 2014, 02:39:02 PM »
Sure you can make it. You need a base for the HCl.
Try 2,6-lutidine in THF, 2,6-lutidine HCl is almost insoluble in THF.
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Offline AlphaScent

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Re: diethylamino trimethylsilane (DEATMS)
« Reply #2 on: June 02, 2014, 03:06:18 PM »
Of course you do.  Would pyridine work??  I dont know if we have lutadine.
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Offline discodermolide

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Re: diethylamino trimethylsilane (DEATMS)
« Reply #3 on: June 02, 2014, 03:15:12 PM »
Yes pyridine will work.
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Offline AlphaScent

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Re: diethylamino trimethylsilane (DEATMS)
« Reply #4 on: June 02, 2014, 03:20:00 PM »
Just need a scavenger.  I should have originally put that.  Thank you for reminding me Disco.

I found some 2,6-lutidine actually.  I knew I had seen it and sure enough there it was.

I will try the lutidine. 

Thanks again!!
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Offline orgopete

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Re: diethylamino trimethylsilane (DEATMS)
« Reply #5 on: June 03, 2014, 12:09:24 AM »
Is probably just use two eq of diethylamine in ether and filter off the hydrochloride.
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