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20th October 2016 @ 22:12
10/18 MRLS 4-2 (0.473 g, 1.4 mmol, 1 equiv) was added to toluene (10 mL) along with MRLS 8-1 (fraction 1, 0.2761 g, 1.5 mmol, 1 equiv), potassium hydroxide (0.3281 g, 5.8 mmol, 4.2 equiv) and 18-crown-6 (0.032 g, 0.12 mmol, 0.09 equiv). The reaction was stirred at room temp for 30 minutes and then heated to 40°C (bath temperature) for 4 h. Planned on leaving stirring at room temperature for only 10 minutes, but problems with hot plate meant lukewarm water for 15 minutes until I got one that worked properly. Came back later that night (11:30) to monitor reaction via TLC. Also noticed that hot plate had stopped heating. TLC showed almost no starting material—I decided to replace the hot plate and keep it stirring over night (~10 more hours) to make sure all starting material had completely reacted. 10/19 TLC showed no SM and baseline spots (tested w/ 60% EtOAc/Hexanes, KMnO4 stain) (shown below). The sample was cooled to room temperature and diluted with 8 mL of water. The mixture was extracted with EtOAc (3 x 20 mL). The combined organic layer was washed with water (2 x 8 mL) until the aqueous layer became neutral. The organic layer was then washed with brine (7 mL) and dried over Na2SO4. The brown/red solution was gravity filtered and dried via rotovap to yield a red brown oil. It was placed under high vac over night. 10/20 Yield: 0.55 g/.6811 80.75% yield Took NMR. Unfortunately, ran out of time so could not run a column on the crude product to verify a successful synthesis. Hopefully, another group will pick up this project!    
Attached Files
TLC 9-1 KMnO4 stain.JPG
MRLS 9-1 proton.pdf