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24th September 2012 @ 07:55
AEW%204-8.png

Potassium tert-butoxide (28 mg, 0.25 mmol, 1.1 eq) was weighed into a round-bottomed flask under Argon. Anhydrous THF (1 mL) was added and the reaction mixture was cooled to 0 ˚C. AEW 3-2 (50 mg, 0.23 mmol, 1 equiv.) was dissolved in THF (3 mL) and added drop wise at 0 ˚C. The reaction mixture was stirred at 0˚C for 10 minutes and then 2-bromoacetamide (32 mg, 0.23 mmol, 1 equiv.) was added in a single portion. The reaction mixture was allowed to stir whilst reaching room temperature for 3 hours. TLC showed SM and spot above (could be decomposition product seen in previous reactions). Reaction mixture allowed to stir at room temperature for a further 2 hours. TLC showed a greater amount of the upper spot. Left to stir at room temperature overnight. The TLC showed a spot beneath the product in addition to the spot above also observed in the SM spotted.

TLC (25% EtOAc in Hexane) after 3 hours:
IMG_0048.jpg


TLC (25% EtOAc in Hexane) after 15 hours:
AEW 4-8 to 4-10 o:n.jpg


TLC (75% EtOAc in Hexane) after 15 hours:
AEW 4-8 to 4-10 o:n 25% EtOAc in hexane.jpg
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IMG_0048.jpg
AEW 4-8.png
AEW 4-8 to 4-10 o:n.jpg
AEW 4-8 to 4-10 o:n 25% EtOAc in hexane.jpg