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Topic: K2CO3 and methanol  (Read 15793 times)

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Offline Elnino

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K2CO3 and methanol
« on: May 07, 2013, 03:25:27 PM »
I was wondering what does K2CO3 in methanol do in this particular reaction attached? I'm not too familiar with these reagents used together.

I figured the K2CO3 would deprotonate the methanol to yield methoxide. The methoxide would react on the carbonyl. Carbonyl would reform kicking off cyclopentoxide anion producing methyl acetate in process

Offline Dan

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Re: K2CO3 and methanol
« Reply #1 on: May 08, 2013, 02:47:06 AM »
I figured the K2CO3 would deprotonate the methanol to yield methoxide. The methoxide would react on the carbonyl. Carbonyl would reform kicking off cyclopentoxide anion producing methyl acetate in process

I would predict the same thing - it's called a transesterification reaction.
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Offline opsomath

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Re: K2CO3 and methanol
« Reply #2 on: May 08, 2013, 10:51:44 AM »
K2CO3 and methanol is a common way to generate a weak methoxide solution, as you said, generally used to remove protecting groups which come off in base. I primarily remember using it to remove a trimethylsilyl group from a terminal alkyne.

In your example, yes, this is a way to take off the acetyl group from that cyclopentanol.

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