반응 #89588

반응 방정식

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

수율 22.0%

용매

dimethylformamide

반응 조건

후처리

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

실험 절차

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.

출처