Reacción #347758

Ecuación de reacción

5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthalenecarbaldehyde

tetrahydrofuran

ammonium chloride

→

captioned compound

5'-Ethyl-3'-methoxy-4'-methoxymethoxy-1'-acetonaphthone

Disolventes

dichloromethane

—

ethyl

methyl lithium

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added at -78° C
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   SecadoThe resultant organic phase was dried with anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled off
5. 5
   Otroto obtain 2.1 g of a brown oily substance
6. 6
   workup.ADDITIONwas added
7. 7
   workup.WAITfollowed by agitation at room temperature for 20 hours
8. 8
   OtroThe insoluble matters were removed by filtration
9. 9
   Concentraciónthe filtrate was concentrated
10. 10
    Otrofollowed by purification by silica gel column chromatography (10% ethyl acetate/hexane)

Procedimiento

2 g of 5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthalenecarbaldehyde was dissolved in 20 ml of absolute tetrahydrofuran, to which 11.5 ml of an ethyl solution of 1.12M methyl lithium was added at -78° C. After 30 minutes, an ammonium chloride aqueous solution was added to the solution and extracted with ethyl acetate. The resultant organic phase was dried with anhydrous magnesium sulfate and the solvent was distilled off to obtain 2.1 g of a brown oily substance. This substance was dissolved in 20 ml of dichloromethane without isolation and purification, to which 30 g of manganese dioxide was added, followed by agitation at room temperature for 20 hours. The insoluble matters were removed by filtration and the filtrate was concentrated, followed by purification by silica gel column chromatography (10% ethyl acetate/hexane) to obtain 1.3 g of the captioned compound as a yellow oily substance.

Fuente