Hydrochloric Acid → HCID 86740123, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropylamine (0.8 g, 8 mmole) was dissolved in tetrahydrofuran (10 ml) under argon, and the solution was cooled at -70° C., followed by adding dropwise 1.6M n-butyl lithium-hexane solution (5 ml) and stirring for 5 minutes. A tetrahydrofuran (2 ml) solution containing methyl 7-phenyl-7-(3-pyridyl)-6-heptenoate (1.19 g, 4 mmole) was added dropwise to the reaction solution. After stirring for 15 minutes under the same reaction conditions, acetone (0.5 ml) was added, and the reaction was carried out for another 10 minutes. Subsequently, 2N hydrochloric acid (5 ml) was added to terminate the reaction, and the temperature of the solution was allowed to rise to room temperature, followed by adding aqueous sodium hydrogencarbonate to adjust to pH 8. The product was extracted with ethyl acetate, and the organic layer was washed with water and dried. The residue was chromatographed on silica gel using isopropyl ether:ethyl acetate (1:1) to yield methyl (E)-2-(1-hydroxy-1-methylethyl)- 7-phenyl-7-(3-pyridyl)-6-heptenoate (5-a) (1.2 g).

Provenance & Evidence