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Experimental

New Zealand's burgoening film industry and gorgeous scenery has made it the home of everywhere from the Narnia to Middle Earth. Check out the latest addition to the experimental film genre: The Synthesis of Molecule 24.

Exposition: The story of the creation of molecule 24 begins in a reaction flask containing compound 23b (4.4 g, 7.5 mmol) in 100 mL methanol at 0 degrees C. To this, a freshly prepared solution of sodium methoxide (2.00 g, 37.5 mmol) in 20 mL methanol was added.

Rising Action: The reaction was stirred for 5 minutes at 0 degrees C, and poured into 200 mL of 1 M aqueous HCl.

The Plot Thickens: The mixture was extracted with ethyl acetate, and the combined organic phase was washed with water, dried over sodium sulfate, and concentrated.
Climax: The residue was purified by column chromatography on silica gel (10% ethyl acetate in hexanes)

Resolution: This afforded molecule 24 (2.90 g, 6.64 mmol, 88% yield).

Glossary of Terms

Organic Phase:  The part of a liquid-liquid extraction mixture containing an organic solvent.  It is typically less dense than water, so it will float on top.  Since most compounds of interest are non-polar, they will dissolve in the aqueous phase.


Washing with Water: When a product mixture contains impurities that build up over the course of the reaction, it’s a good idea to “wash” them with a solvent that ideally dissolves the impurities, but not the target product.


Drying:  In this case, drying refers to the removal of water, not all liquid.  It is accomplished by the addition of a desiccant, which is a hygroscopic agent used as a drying agent.