Reaktion #89588

Reaktionsgleichung

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

Ausbeute 22.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle