10 equivalents (.78 mL of 1M) of BBr3 in CH2Cl2 was added to a solution of
3 (in CH2Cl2, .078mmol) at -78oC. The solution was warmed to room temperature, 23oC, while being stirred for 1.5 hours. Then, 2mL of .5M, pH neutral, KH2PO4/K2HPO4 (in distilled water, a buffer solution) was added. The compound was then separated by a
sep funnel using 3 sets of 15mL ethyl acetate. The recovered materials were dried using
MgSO4 (a dessicant), run through a
vacuum filtration to separate the solid out, which is then concentrated. 1mL of Acetic anhydride and pyridine in a 1:1 volume ratio was added immediately, and then the solution was stirred at 23oC for 3 hours. The resulting product was purified via
flash column chromatography using silica gel and a 4:1 mix of hexane to ethyl acetate, ending with 37mg of
15, 67% yield.
When you are the Earth Shaker, the Lord of the Seas, and among the Eldest of the Gods, even riding around in your snazzy dolphin chariot can get old. Since that got old a few milennia ago, Poseidon decided to stave off the boredom by explaining exactly how the synthesis of 15 from 14 happened. Here's what he found (no earthquakes included).
