반응 #2195478

반응 방정식

3,4-Dihydroxybenzaldehyde

Cesium carbonate

Oleyl mesylate

→

yellow oil

수율 89.2%

Dioleyloxybenzaldehyde

수율 89.2%

용매

diglyme

반응 조건

후처리

1. 1
   기타sealed
2. 2
   기타flushed with argon
3. 3
   온도The reaction mixture was cooled to room temperature
4. 4
   여과filtered
5. 5
   세척The solids were washed with 1,2-dichloroethane
6. 6
   농축The combined filtrate and washes were concentrated
7. 7
   기타dried under high vacuum at 65° C.
8. 8
   기타to remove residual diglyme
9. 9
   기타The resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes)

실험 절차

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.

출처