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4th March 2013 @ 20:57

Repeat of AT-5-1.

To AT-1 (1.55 g, 8.79 mmol, 1.00 equiv.) in THF (100 mL) at -78 C was added n-BuLi (7.03 mL, 2.5 M in hexanes, 17.6 mmol, 2.00 equiv.) dropwise with stirring. The reaction mixture was allowed to stir at -78 C for 30 minutes, after which bromine (1.35 mL, 4.21 g, 26.4 mmol, 3.00 equiv.) was added. The reaction mixture was warmed to rt and stirred for 30 minutes. The reaction mixture was diluted with an aqueous solution of sodium thiosulfate (100 mL) and extracted into ethyl acetate (3 x 75 mL). The combined organic extracts were washed with water (100 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography (8:1 hexanes:ethyl acetate) to give recovered starting material AT-1 (0.530 g, 35%) and product AT-5 (0.455 g, 32% based on RSM). 

 

HIRAC

AT-5-1.pdf

 

NMR

AT-5-2-product.pdf
1H NMR spectrum of product AT-5.

AT-5-2-startingmaterial.pdf
1H NMR spectrum of starting materal AT-1.

AT-5-2-13C.pdf
13C{1H} NMR spectrum of AT-5.
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Attached Files
AT-5-1.pdf
AT-5-2.jpg
AT-5-2-startingmaterial.pdf
AT-5-2-product.pdf
AT-5-2-13C.pdf