Reaktion #11504

Reaktionsgleichung

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

Lösungsmittel

ethyl acetate

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle