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2nd November 2017 @ 21:07

Reaction for SGS17-7-1

Crude 2-(3,5-bis(trifluoromethyl)phenyl)-3-oxopentanenitrile (SGS17-4-1) (approx. 5 g, 0.02 mol max. depending on purity) was dissolved in a mixture of toluene (75 mL) and 2-mthylpropan-1-ol (7 mL, 0.08 mol). 15 drops of 18 M sulfuric acid was added to the mixture, which was then refluxed for 7 h, left at room temperature over the weekend and refluxed for a further 7 h.

At the end of the reflux the reaction mixture was orange.  4 mL of triethylamine was added to neutralise the sulfuric acid, and the mixture turned red immediately.  Chromatography silica (10 g) was added to the mixture and stirred overnight.  An initial TLC in DCM was done showing the presence of a number of different compounds.

TLC of SGS17-7-1 against starting material (SGS17-4-1)

TLC of SGS17-7-1 against starting material (SGS17-4-1)

The mixture was left to evaporate, and a red oil was produced.  A sample was sent to the Univerisity of Sydney for NMR.

Reaction performed by: James Arnall, Kieran Connor, Alex Crawford, Duncan Currie, Oliver Hervir, Hugo McCahon-Boersma, Harry Thawley, Erin Sheridan