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DIASTEREOSELECTIVE ALDOL CONDENSATION USING A CHIRAL OXAZOLIDINONE AUXILIARY: (2S*,3S*)-3-HYDROXY-3- PHENYL-2-METHYLPROPANOIC ACID - Essay Example

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The first step of this procedure is to add 17.7 g of (S)-4-(phenylmethyl)-2-oxazolidinone into a 500ml flask, which is then capped with rubber septum. Nitrogen is used for flushing the compound. A cannula is then used to add anhydrous tetrahydrofuran to the flask. At this point,…
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DIASTEREOSELECTIVE ALDOL CONDENSATION USING A CHIRAL OXAZOLIDINONE AUXILIARY: (2S*,3S*)-3-HYDROXY-3- PHENYL-2-METHYLPROPANOIC ACID
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"DIASTEREOSELECTIVE ALDOL CONDENSATION USING A CHIRAL OXAZOLIDINONE AUXILIARY: (2S*,3S*)-3-HYDROXY-3- PHENYL-2-METHYLPROPANOIC ACID"

Download file to see previous pages Then the solution is put in a reaction flask for a period of 10 minutes. During or after this time, the solution’s color could become yellow as well as slightly cloudy.The third step is the addition of 9.6 mL of propionyl chloride into the butyllithium solution by the use of a syringe. After this addition, the resulting solution is usually clear and almost colorless. This solution is stirred for a period of 30 min while it is still at the -70 C. After stirring, the temperature of the solution is then increased to an ambient temperature over a period of 30 minutes. In order to quench any excessive propionyl chloride, a 60 mL solution of saturated ammonium chloride should be added to the above solution. Similarly, any excess tetrahydrofuran and hexane should also be removed by the use of a rotary evaporator, which should be at temperatures of between 250 – 300 C. Then the suspension that results is extracted by the use of dichloromethane in two 80 mL portions. These extracts are then washed in a solution of 75mL 1M sodium hydroxide as well as a solution of 75mL brine. Anhydrous sodium sulfate is then used to dry the extracts, before filtration. In order to remove the solvent, rotary evaporation is used. After this removal, a residue that is an oil of light yellow color is left and it is crystallized by placing it in a refrigerator overnight. Once the crystalline solid is obtained, it should be pulverized as well as triturated using the least possible amount of cold hexane. Once filtration and drying are done, a quantity of between 21.2 – 22.3 g, which is equivalent to 91% - 96%, of the product that should result from this procedure is obtained in the form of a crystalline solid. This solid is usually colorless.
The first step involves the addition of 21.2g of acylated oxazolidinone into a 2L flask, which should be dry and should have a large magnetic bar for stirring purposes. Rubber septum is also used to seal the flask whereas ...Download file to see next pagesRead More
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