Reacción #684957

Ecuación de reacción

water

N,N-diisopropylethylamine

chloromethyl methyl ether

4-benzyloxy-2-hydroxybenzaldehyde

N,N-diisopropylethylamine

chloromethyl methyl ether

→

title compound

4-Benzyloxy-2-(methoxymethoxy)benzaldehyde

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaunder reflux for 19 hours
3. 3
   workup.STIRRINGthe resulting mixture was stirred
4. 4
   Temperaturaheated
5. 5
   Temperaturaunder reflux for another 10 hours
6. 6
   Extracciónthe reaction mixture was extracted with ethyl acetate
7. 7
   Lavadowashed with a saturated aqueous ammonium chloride solution and saturated brine
8. 8
   Secadodried over anhydrous magnesium sulfate
9. 9
   Filtraciónfiltered through silica gel and alumina
10. 10
    ConcentraciónThe filtrate was concentrated under reduced pressure

Procedimiento

N,N-diisopropylethylamine (1.98 ml) and chloromethyl methyl ether (0.76 ml) were added to a solution of 4-benzyloxy-2-hydroxybenzaldehyde (2071 mg) in tetrahydrofuran (30 ml), and this reaction mixture was stirred and heated under reflux for 19 hours. N,N-diisopropylethylamine (2.7 ml) and chloromethyl methyl ether (1.04 ml) were further added, and the resulting mixture was stirred and heated under reflux for another 10 hours. After water was added, the reaction mixture was extracted with ethyl acetate, washed with a saturated aqueous ammonium chloride solution and saturated brine, dried over anhydrous magnesium sulfate, then filtered through silica gel and alumina. The filtrate was concentrated under reduced pressure to give the title compound (2470 mg). This compound was used in the following reaction without further purification.

Fuente