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7th December 2012 @ 04:33
Reaction Scheme

Crude AEW 3-5 (~0.92 mmol, 1 equiv) was dissolved in MeCN (5 mL) at 0˚C and NaH (60% dispersed in mineral oil, 44 mg, 1.1 mmol, 1.2 equiv.) was added and the reaction mixture stirred at 0 ˚C for 30 minutes. Bromoacetonitrile (73 microlitres, 1.1 mmol, 1.2 equiv.) was added at 0 ˚C and the reaction mixture stirred for 5 minutes prior to the removal of the ice bath. Reaction mixture stirred whilst reaching room temperature for 2 hours. TLC showed no reaction. Stirred over the weekend. Water added to quench, acetonitrile removed under reduced pressure and then aqueous layers extracted with DCM (x2), washed with brine, dried (MgSO4), filtered and evaporated to give a dark brown oil. 1H NMR showed only starting material. Crude reaction mixture saved for a second attempt.

Hazard and Risk Assessment:
AEW 28-1.pdf

Crude 1H NMR:
Attached Files
AEW 28-1.png
AEW 28-1.pdf