Diisopropyl Ether → 1(RS) [1-(2-propynyl)-2-trifluoromethyl-(1H)-indol-3-yl]-prop-2-ynyl alcohol

Participants

Reaction Conditions

Reaction Steps

4.5 g of 1-(2-propynyl)-2-trifluoromethyl-3-formyl-(1H)-indole in 30 ml of tetrahydrofuran were cooled at -15° C. and over 15 minutes, 26 ml of a solution of magnesium ethynyl bromide in tetrahydrofuran (0.8M ) were added. After stirring for one hour at -5° C., another 5 ml of magnesium solution were added, and the mixture was allowed to return to ambient temperature. After stirring for 30 minutes and then pouring into a saturated aqueous solution of monosodium phosphate, extraction was carried out with isopropyl ether. The solvent was eliminated under reduced pressure to obtain 5.89 g of crude product which was purified by chromatography over silica (eluent: hexane-ethyl acetate 9-1) to obtain 1.91 g of 1(RS) [1-(2-propynyl)-2-trifluoromethyl-(1H)-indol-3-yl]-prop-2-ynyl alcohol melting at 98° C.

Provenance & Evidence