Reaktion #11508

Reaktionsgleichung

water

2-methyl-4-trifluoromethylsulfoxyindole

acrylic acid methyl ester

diisopropylethylamine

→

title compound

3-(2-Methylindol-4-yl)acrylic acid methyl ester

Lösungsmittel

ethyl acetate

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

To a solution 2-methyl-4-trifluoromethylsulfoxyindole (3.2 g; prepared in Reference Example 2) in N,N-dimethylformamide (50 ml) was added acrylic acid methyl ester (2.24 ml), diisopropylethylamine (5.9 ml) and dichlorobis(triphenylphosphine)palladium(II) (238 mg), and the mixture was stirred at 95° C. for 2 days. To the reaction mixture was added water and ethyl acetate, 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 (950 mg) having the following physical data.

Quelle