Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → methyl trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylate

Participants

Reaction Steps

As in Example 226, the impure 3-(4-fluorophenyl)- 1-(1-methylethyl)-1H-indole-2-carboxaldehyde (5.56 g) from the previous example was reacted in methanol (75 mL) with (carbomethoxymethylene)triphenylphosphorane (6.2 g) was stirred at room temperature for 1 hour. The pale yellow solids that formed were filtered and washed with cold methanol to furnish 4.58 g of (E)-3-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-2-propenoic acid methyl ester. A sample was crystallized from dichloromethane-hexane to yield the analytical specimen, mp 155°-157° C.

Provenance & Evidence