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25th March 2013 @ 05:45

Performed concurrently with AT-5-6. 

 

 

To AT-5 (2.00 g, 11.7 mmol, 1.0 equiv.) in THF (120 mL) at -78 C was added n-BuLi (7.03 mL, 17.6 mmol, 1.5 equiv.) dropwise and the reaction mixture stirred at -78 C for 30 minutes. Bromine (1.20 mL, 23.4 mmol, 2.0 equiv.) was added dropwise and the reaction mixture warmed to rt and stirred for 1 h. 

The reaction mixture was diluted with an aqueous solution of sodium thiosulfate (150 mL) and extracted into ethyl acetate (3 x 100 mL). The combined organic extracts were dried (MgSO4), concentrated under reduced pressure and the residue purified by flash column chromatography (7:1 hexanes:ethyl acetate) to give the product AT-5 (1.65 g, 56%).

 

HIRAC

AT-5-1.pdf
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AT-5-1.pdf
AT-5-5.jpg