반응 #11504

반응 방정식

4-butoxybenzoyl chloride

water

2-methyindole-4-carboxylic acid benzyl ester

sodium hydride

→

title compound

1-(4-Butoxybenzoyl)-2-methylindole-4-carboxylic acid benzyl ester

용매

ethyl acetate

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature overnight
2. 2
   기타separated
3. 3
   추출The aqueous layer was extracted with ethyl acetate
4. 4
   세척The combined organic layer was washed with water
5. 5
   건조a saturated aqueous solution of sodium chloride, successively, dried
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was purified by column chromatography on silica gel (hexane-ethyl acetate)

실험 절차

To a solution of 2-methyindole-4-carboxylic acid benzyl ester (690 mg; prepared in Reference Example 11) in N,N-dimethylformamide (8 ml) was added sodium hydride (114 mg; 60%) at 0° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was added 4-butoxybenzoyl chloride (0.54 ml), and the mixture was stirred at room temperature overnight. To the reaction mixture was added water and ethyl acetate, and then separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and a saturated aqueous solution of sodium chloride, successively, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane-ethyl acetate) to give the title compound (1.02 g) having the following physical data.

출처