Hydrochloric Acid → HCID 86589630, compound

Participants

Reaction Conditions

Reaction Steps

680 mg of 6-(diethoxyphosphoryl)-3-methyl-hexa-2,4-dienoic acid ethyl ester were dissolved in 10 ml of THF and treated dropwise with 2.25 ml of a 1 molar solution of lithium bis(trimethylsilyl)amide in hexane at −78° C. After 10 minutes of stirring, a solution of 500 mg of 4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene-2-carbaldehyde in 5 ml of THF was added dropwise at −78° C. The reaction mixture was slowly warmed to −40° C. and kept at this temperature for 3 hours. The cold reaction mixture was poured in ice/water, acidified with 1 N HCl and extracted with ether. The organic phase was washed with water, dried (Na2SO4) and the solvent was evaporated. The crude oil was purified with medium pressure chromatography (silica gel, hexane/tert.-butyl methyl ether 1%) to give 250 mg of pure (2Z, 4E, 6E)-3-methyl-7-(4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-inden-2-yl)-hepta-2,4,6-trienoic acid ethyl ester and 400 mg of (2E, 4E, 6E)-3-methyl-7-(4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-inden-2-yl)-hepta-2,4,6-trienoic acid ethyl ester as colorless oils.

Provenance & Evidence