Experimental Design

Production of Compound 46: Compound 59 (2.47 g, 12.7 mmol) was azeotroped. In a flame-dried flask, triphenylphosphine (3.33 g, 12.7 mmol) was dissolved in dry THF (50 mL).

N-chlorosuccinimide (1.70 g, 12.7 mmol, 1.0 equiv.) was added to the solution. It was stirred for 30 minutes. Compound 59 was dissolved in dry THF (50 mL).

Then the previous mixture of triphenylpphosphine and NCS were added. This reaction was left to sit and stir for 18 hours. The solvent was then removed in vacuo.

The residue was dissolved in DCM (200 mL), washed with water (3 x 150 mL), then brine (150 mL), and finally dried (MgSO4). The solvent was removed in vacuo.

The crude material was purified by flash column chromatography (silica gel, 5:1 hexanes:DCM) to give pure compound 46 (1.49 g, 55%).

- Azeotrope : An azeotrope is a mixture of two or more liquids that its composition cannot be changed by simple distillation.

The reason this occurs is because when the azeotrope is boiled, the same ratio of liquids is evaporated

- DCM: Dichloromethane is a highly used solvent that is capable of dissolving many organic solutes.

- In Vacuo: The Latin term in vacuo is also used to describe an object as being in what would otherwise be a vacuum

-N-chlorosuccinimide (NCS): a mild oxidant (oxidating reagent that gains electrons through an oxidation reaction LEO goes GER) that is used in chlorination reactions.

(Chlorination being the process of adding chlorine to water)

NCS

- THF: Tetrahydro Furan

THF

- Triphenylphosiphine