Reacción #66664

Ecuación de reacción

sodium hydride

sodium 5-iodo-2-acetyl,4-methoxyphenol

chloromethoxy methane

→

1-(2-hydroxy-4-iodo-5-methoxy-phenyl)-ethanone

Rendimiento 107.5%

Disolventes

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónAfter 30 minutes the mixture was extracted with CH2Cl2
2. 2
   LavadoThe The combined organics were washed with brine
3. 3
   Secadodried over Na2SO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroPurification via flash chromatography (88:12=hexane/ethyl acetate)

Procedimiento

To suspension of sodium hydride (0.044 g, 1.1 mmol, 60% in mineral oil) in 0.5 ml DMF was added sodium 5-iodo-2-acetyl,4-methoxyphenol (0.292 g, 1 mmol, prepared as described in Example 35) as a solution in 1.5 ml DMF. After 10 minutes chloromethoxy methane (0.079 g, 1.0 mmol) was added. After 30 minutes the mixture was extracted with CH2Cl2. The The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (88:12=hexane/ethyl acetate) afforded 1-(2-hydroxy-4-iodo-5-methoxy-phenyl)-ethanone (0.314 g, 85%) as yellow solid; [MH]+=337.

Fuente