反応 #2195478

反応方程式

3,4-Dihydroxybenzaldehyde

Cesium carbonate

Oleyl mesylate

→

yellow oil

収率 89.2%

Dioleyloxybenzaldehyde

収率 89.2%

溶媒

diglyme

反応条件

後処理

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

実験手順

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.

出典