HCID 18642346, compound → HCID 86746019, compound

Participants

Reaction Steps

760 mg of (1R,4S,5S,8R)-4,8-dimethyl-7-oxo-2,3-dioxabicyclo[3.3.1]nonane-4-carboxaldehyde are dissolved in 80 ml of methylene chloride. 2.5 g of 2,7-bis(trifluoromethyl)quinolin-4-yl-methylidenetriphenylphosphorane are added thereto and the solution is left to stand at room temperature for 24 hours. The methylene chloride is distilled off and the residue is separated into the (E)- and (Z)-isomers by column chromatography on silica gel while eluting with methylene chloride. After crystallization from hot methanol there are obtained (1R,4S,5S,8R)-4-[(Z)-2-[2,7-bis(trifluoromethyl)-4-quinolinyl]vinyl]-4,8-dimethyl-2,3-dioxabicyclo[3.3.1]nonan-7-one as white crystals [m.p. 160°; [α]D25 =53.7° (c=1 in ethanol)] and (1R,4S,5S,8R)-4-[(E)-2-[2,7-bis(trifluoromethyl)-4-quinolinyl]vinyl]-4,8-dimethyl-2,3-dioxabicyclo[3.3.1]nonan-7-one [m.p. 188°].

Provenance & Evidence