Реакция #2075686

Уравнение реакции

3,4-Dihydroxybenzaldehyde

Cesium carbonate

Oleyl mesylate

→

yellow oil

Выход 89.2%

Dioleyloxybenzaldehyde

Выход 89.2%

Растворители

diglyme

Условия реакции

Обработка

1. 1
   Другоеsealed
2. 2
   Другоеflushed with argon
3. 3
   ТемператураThe reaction mixture was cooled to room temperature
4. 4
   Фильтрацияfiltered
5. 5
   ПромывкаThe solids were washed with 1,2-dichloroethane
6. 6
   КонцентрированиеThe combined filtrate and washes were concentrated
7. 7
   Другоеdried under high vacuum at 65° C.
8. 8
   Другоеto remove residual diglyme
9. 9
   ДругоеThe resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes)

Методика

3,4-Dihydroxybenzaldehyde (2.76 g, 20.0 mmol) was weighed into a 200 mL round bottomed flask with a stir bar. The flask was charged with diglyme (100 mL), septum sealed and flushed with argon. Cesium carbonate (19.5 g, 60.0 mmol) was added to the solution slowly in portions. Oleyl mesylate (15.2 g, 44.0 mmol) was added via syringe. The reaction mixture was heated to 100° C. under slight positive pressure of argon. The reaction mixture was cooled to room temperature and filtered. The solids were washed with 1,2-dichloroethane. The combined filtrate and washes were concentrated and then dried under high vacuum at 65° C. to remove residual diglyme. The resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes) to afford 11.4 g (89%) of a yellow oil that turned to yellow wax upon standing at room temperature.

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