The Iceberg Bar

Relax, get a nice drink, and enjoy your cruise. Our bartenders are so amazing they've got bartending down to a science! Our drinks are nice and smooth like your cruise, and chilled too like all these icebergs showing up all of a sudden. Our captain rates the Iceberg Bar 11/10!!! Get your drinks quick!

 

A solution of molecule 7 (43.06 g, 132.7 mmol, 1.0 equiv) in THF (650 mL) was added in one portion to a stirred suspension of molecule 6 (39.60 g, 132.7 mmol, 1.0 equiv) and lithium chloride (8.44 g, 199.1 mmol, 1.5 equiv) in THF (650 mL) at 0 °C.  Triethylamine (20.3 mL, 146.0 mmol, 1.1 equiv) was added dropwise, and the resulting tan suspension was stirred at 0 °C for 15 min, then at 40 °C for 2.5 h.  Once TLC indicated completion, the reaction was quenched with saturated ammonium chloride solution (300 mL) and the mixture was extracted with EtOAc (3 x 375 mL).  The combined organic phases were washed with saturated brine (375 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified via flash chromatography on silica gel (10% to 50% EtOAc/hexanes) to give enone 8 (59.1 g, 90% yield) as a yellow-orange oil. A yellow-orange oil? Sounds Delish!!!- Captain Edward J. Smith