HCID 69760555, compound → HCID 9953506, compound

Participants

Reaction Steps

19.2 g of 4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid 4-allyloxycarbonyl-phenyl ester were dissolved in 460 ml of THF. The reaction flask was evacuated and ventilated with argon twice. 4.6 g of tetrakis (triphenylphosphine) palladium were added, followed by 37 g of morpholine. The reaction mixture was stirred for 4 hours at room temperature, poured on 1500 ml of ice/water, acidified with 6N HCl and extracted with ethyl acetate. The organic phase was washed with water, dried over Na2SO4 and evaporated to yield a yellow solid. Purification by column chromatography (SiO2, hexane/ethyl acetate=1:3) and crystallization from ethyl acetate/hexane afforded 12.9 g of 4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid 4-carboxy-phenyl ester, m.p. 156-158° C.

Provenance & Evidence