Reacción #2075686

Ecuación de reacción

3,4-Dihydroxybenzaldehyde

Cesium carbonate

Oleyl mesylate

→

yellow oil

Rendimiento 89.2%

Dioleyloxybenzaldehyde

Rendimiento 89.2%

Disolventes

diglyme

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrosealed
2. 2
   Otroflushed with argon
3. 3
   TemperaturaThe reaction mixture was cooled to room temperature
4. 4
   Filtraciónfiltered
5. 5
   LavadoThe solids were washed with 1,2-dichloroethane
6. 6
   ConcentraciónThe combined filtrate and washes were concentrated
7. 7
   Otrodried under high vacuum at 65° C.
8. 8
   Otroto remove residual diglyme
9. 9
   OtroThe resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes)

Procedimiento

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.

Fuente