video tutorial Synthesis of sodium ethyl nitrophenylpyruvate

Summary of the procedure and findings:

• A strong base deprotonates ortho-nitro-toluene at the benzylic methyl, generating a nucleophile that adds to diethyl oxalate and eliminates ethanol to form the sodium salt of ethyl ortho-nitro phenyl pyruvate.
• Traditionally, potassium ethoxide is used, but this setup uses sodium ethoxide formed from sodium metal; adding a small amount of methanol to ethanol improves ethoxide solubility and keeps the mixture liquid.
• Reaction setup and solvents: dry glassware, an ethanol/diethyl ether solvent mix, nitro-toluene dissolved in diethyl ether, and diethyl oxalate added with an exotherm, followed by vigorous stirring and a brief reflux.
• Workup and isolation: after crystallization, filtration is improved by using a glass filter; the product is dried with diethyl ether assistance.
• Yield: about 26.5 g of the sodium salt (26.5 g from 18 g of nitrotoluene, roughly 78% yield).
• Product and future work: the sodium salt of ethyl ortho-nitro phenyl pyruvate could be reduced to an amine and react with the carbonyl to form a new heterocycle (indole-related), potentially decarboxylating to indole upon heating; the team plans to explore this path.