反应 #2075686

反应方程式

3,4-Dihydroxybenzaldehyde

Cesium carbonate

Oleyl mesylate

→

yellow oil

收率 89.2%

Dioleyloxybenzaldehyde

收率 89.2%

溶剂

diglyme

反应条件

后处理

1. 1
   其他sealed
2. 2
   其他flushed with argon
3. 3
   温度The reaction mixture was cooled to room temperature
4. 4
   过滤filtered
5. 5
   洗涤The solids were washed with 1,2-dichloroethane
6. 6
   浓缩The combined filtrate and washes were concentrated
7. 7
   其他dried under high vacuum at 65° C.
8. 8
   其他to remove residual diglyme
9. 9
   其他The resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes)

实验过程

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.

来源