Reacción #89588

Ecuación de reacción

Ethyl 5-bromovalerate

Sodium hydride

1-(1H-indol-3-yl)-2-(2-methoxyphenyl)ethanone

→

ethyl 5-(3-(2-(2-methoxyphenyl)acetyl)-1H-indol-1-yl)pentanoate

Rendimiento 22.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONafter the addition
2. 2
   workup.STIRRINGthe reaction mixture was stirred at room temperature overnight
3. 3
   OtroThe solvents were removed in vacuo
4. 4
   Extracciónextracted three times with ethyl acetate (3×50 ml)
5. 5
   Secadodried over sodium sulphate
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe residue was purified by column chromatography (silica gel, 20% ethyl acetate in hexane)

Procedimiento

60% Sodium hydride in mineral oil (480 mg, 12 mmol) was suspended in dimethylformamide (50 ml) and 1-(1H-indol-3-yl)-2-(2-methoxyphenyl)ethanone 3 (2.66 g, 10 mmol) was added portionwise at room temperature, allowing to stir further 45 min at room temperature after the addition was finished. Ethyl 5-bromovalerate (2.37 ml, 15 mmol) was added dropwise at room temperature and the reaction mixture was stirred at room temperature overnight. The solvents were removed in vacuo and the residue was taken into water (30 ml) and extracted three times with ethyl acetate (3×50 ml). The organic fractions were combined and dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 20% ethyl acetate in hexane) to give 856 mg (22%) of ethyl 5-(3-(2-(2-methoxyphenyl)acetyl)-1H-indol-1-yl)pentanoate (Ethyl N-(carboxybutyrate) JWH-250) 7 as a semi solid.

Fuente