Reacción #3781

Ecuación de reacción

Triphenylphosphine ethylbromide

sodium hydride dimethyl sulfoxide

4,6-dimethoxy-2-hydroxybenzaldehyde

→

3,5-dimethoxy-2-propylphenol

Rendimiento 46.4%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat 50° C.
2. 2
   Otroovernight
3. 3
   OtroAfter the termination of the reaction
4. 4
   Otrothe resulting solution was partitioned with ethyl acetate and dilute hydrochloric acid
5. 5
   Lavadothe resulting ethyl acetate phase was washed in water and subsequently in a saturated sodium chloride solution
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONto distill off the solvents under reduced pressure
8. 8
   OtroThe residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=3:1)
9. 9
   workup.ADDITIONfollowed by addition of a catalytic amount of platinum dioxide for hydrogenation

Procedimiento

Triphenylphosphine ethylbromide (4.1 g) was added to a 2N sodium hydride/dimethyl sulfoxide solution (11 ml), prior to agitation at 50° C. for 30 minutes. To the mixture was added 4,6-dimethoxy-2-hydroxybenzaldehyde (1 g), for agitation at 50° C. overnight. After the termination of the reaction, the resulting solution was partitioned with ethyl acetate and dilute hydrochloric acid, and the resulting ethyl acetate phase was washed in water and subsequently in a saturated sodium chloride solution and dried over anhydrous magnesium sulfate, to distill off the solvents under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=3:1), followed by addition of a catalytic amount of platinum dioxide for hydrogenation, to recover 3,5-dimethoxy-2-propylphenol (0.5 g; yield of 46%). By 1H-NMR (90 MHz, CDCl3), the compound has the peaks shown below.

Fuente