[Erythromycin]

I'm trying to condense phenylpropionate into the corresponding beta keto ester. My yields are 5-15%. I have tried using both LDA and sodium hydride, varying the molar ratios of each. I have also tried temperatures up to 100 C. I do the work-up with acid following the reaction. Are there any Claisen experts out there who can help me? Thank you!

[russellm72]

Haven't done one since i was doing my undergraduate studies and it wasn't self condensation. I used NaOMe/MeOH at reflux.

Have u checked the condition of your phenyl propionate? NMR and made sure its dry. I'm guessing its an oil and if so have u distilled it fresh prior to use.

R.