Phosphorus oxychloride → 1-(5-Methoxy-1-methyl-1H-indol-3-yl)ethan-1-one

반응식

P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[CH:12]=[CH:11]2.[CH3:18][C:19](N(C)C)=[O:20]>>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[CH:12]=[C:11]2[C:19](=[O:20])[CH3:18]

참가 물질

반응물 3

HCID 24813Phosphorus oxychloride

HCID 31374Dimethylacetamide2회

HCID 8198645-methoxy-1-methyl-1H-indole

생성물 1

HCID 212700281-(5-Methoxy-1-methyl-1H-indol-3-yl)ethan-1-one

실험 절차

Phosphoryl chloride (1.05 ml) was added dropwise to ice-cooled dimethylacetamide (10 ml) and the solution was stirred, in ice, for 5 min. A solution of 5-methoxy-1-methyl-1H-indole (1.4 g) in dimethylacetamide (5 ml) was added dropwise, and the resulting solution was stirred at 85° for 2 h, then cooled, and partitioned between sodium carbonate (2N; 100 ml) and ethyl acetate (2×100 ml). The combined organic extracts were washed with water (2×100 ml), dried and evaporated in vacuo. The residue was purified by FCC eluting with ethyl acetate to give a solid which was crystallised from a mixture of ethyl acetate and hexane to give the title compound (0.6 g), m.p. 167°-168°.