THF is a colorless liquid that is used as a monomer, chemical intermediate, and a commercial solvent. THF functioned as the solvent in this synthesis.

Corma, A.; Iborra, S.; Velty, A. Chemical Reviews, 2007, 107, 2411-2502.

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Sodium methoxide is a very basic solid that catalyzes many reactions (i.e. condensations, dehydrohalogenations) and acts as a nucleophile in SN2 reactions. It is a flammable solid that can combust at 70-80° C. In this reaction, sodium methoxide deprotonated a hydrogen in the first step in the epimerization reaction.

Sodium Methoxide. e-EROS Encyclopedia of Reagents for Organic Synthesis [online]; Wiley & Sons, Posted September 15, 2006.

http://onlinelibrary.wiley.com/doi/10.1002/047084289X.rs089m.pub2/abstract (accessed Mar 28, 2014)

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Methanol is used widely both in the lab and industrially. The largest use of methanol is in the production of methyl t-butyl ether (MTBE), which is a gasoline additive. Other uses of methanol are in dimethyl terephthalate, methylamines, chloromethanes, and methyl methacrylate. Additionally, methanol is often used as a solvent in car windshield wash, wall paints, and aerosol spray paint. In this reaction, methanol was used to protonate the carbanion in the second step of the epimerization reaction.

U.S. Environmental Protection Agency; Chemical Summary for Methanol. EPA 749-F-94-013a. 1994.

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Sodium hydroxide is a colorless noncombustible solid. Also known as lye, this extremely caustic reagent should be kept out of contact with water, as it can generate sufficient heat to ignite combustible materials. This reagent was used during the second reaction (acyl transfer)

Sodium Hydroxide. NIOSH Pocket Guide to Chemical Hazards [online]; Centers for Disease Control and Prevention, Posted November 18, 2010.

 http://www.cdc.gov/niosh/npg/npgd0565.html (accessed Mar 31, 2014)

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Ethanol is a clear, colorless liquid. Ethanol is easily absorbed by the human gastrointestinal tract and has antibacterial qualities. In the lab, ethanol is a common solvent and preservative. In this reaction, ethanol is the conjugate acid of the leaving group produced in the acyl transfer reaction.

Ethanol. PubChem Compound [online]; National Center for Biotechnology Information, posted no date cited.

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=702 (accessed Mar 31, 2014)

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Hydrochloric acid is an extremely corrosive acid that is often used as a laboratory reagent. The most common way to synthesize hydrochloric acid is by dissolving hydrogen chloride in water. Additionally, hydrochloric acid is present in human gastric juices. In this reaction, HCl functioned in the acidic workup to make sure the product was protonated and not its conjugate base.

HCl. PubChem Compound [online]; National Center for Biotechnology Information, posted no date cited.

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=313 (accessed Mar 31, 2014)

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Ethyl acetate is a common solvent used industrially for agrochemicals, inks, cosmetics, and adhesives. Although it is extremely flammable, it is not classified as dangerous for the environment. In this reaction, ethyl acetate was used in the extraction of product 18.

Rhodia: Member of the Solvay Group. http://www.solvay.com/en/binaries/Ethyl_acetate_GPS_rev0_June12_RHD-139545.pdf

(accessed April 1 2014)

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Sodium sulfate is typically used as a drying agent in organic reactions. In nature, sodium sulfate occurs as mirabilite and thernadite deposits near salt lakes. Sodium sulfate is neutral and the anhydrous salt readily absorbs moisture. Industrially, sodium sulfate is used in laundry, dishwashing agents, and detergents.

Etacude: Sodium Sulfate, http://chemicals.etacude.com/s/sodium_sulfate.php (accessed April 1 2014)

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