3-Trifluoroacetyl-5-methoxy-2-methylindole → Ethyl 3-(5-methoxy-2-methylindol-3-yl)-4,4,4-trifluoro-2-butenoate

Participants

Reaction Conditions

Reaction Steps

A suspension of the indole from Step 1 (18.3 g, 71.4 mmol) and carbethoxy-methylenetriphenylphosphorane (49.7 g, 142.8 mmol) in 100 mL of toluene was pressurized to 900 psi nitrogen in a stainless steel, high pressure Parr reactor and was heated to 120° C. for 39 h. The reaction mixture was cooled, concentrated and purified by flash chromatography (30% ethyl acetate/hexanes) to give 23 g of the title compound as a mixture of E- and Z- isomers.

Provenance & Evidence