[qwaszx]

Hello There!

I tried to make the TADDOL shown in the attached file by double addition of an aryl Grignard to the acetonide methyl ester. This is a lit compound.

After column chromatography, I recorded 19F, 1H, and 13C spectra. I expected to see quartets showing C-F coupling in the 13C spectrum (500 MHz). However, I can only find triplets.

The 1H AND 19F look just about as I anticipated.

Can someone help me figure out why I didn't make the expected product or why my 13C spectrum is not showing quartets?

[blaisem]

I'm no expert, but are the ¹³C spectra proton-decoupled?

If yeah, then no idea...there's nothing else for the carbon to really couple with, so no idea where a 1:2:1 would be from.

[Dan]

Any chance you can post the spectra?