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EXPERIMENTAL PROCEDURE

 

A solution of dimethyl-1-diazo-2-oxopropylphosphonate and the aldehyde 12 in methanol is created and the potassium carbonate is added at 0°C under argon atmosphere. The mixture is stirred for 2.5 hours. Aqueous saturated ammonium chloride and pentane were then added. The organic layer was separated, dried with sodium sulfate, and evaporated. An 88% yield of acetylene 13 was collected using column chromatography on silica gel.

Rotary Evaporation: a method for distilling the product by evaporating off any remaining solvent using a rotary evaporator. The rotary evaporator spins the solution in a water bath under a vacuum.The solution should not be allowed to evaporated completely, but should be removed after a reasonable amount of time has passed to evaporate the solvent.
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