HCID 69315922, compound → HCID 69318208, compound

Participants

Reaction Conditions

Reaction Steps

Butyllithium (1.6 ml, 1.5 M) was added dropwise to a solution of 6-bromo-8-fluoro-3,4-dihydrocoumarin (4.8 g) in THF (50 ml) as cooled at −100° C. in an argon gas stream. After completion of the dropwise addition, the temperature of the reaction mixture was raised to −78° C., and a solution of zinc bromide (5 g) in THF (100 ml) was added dropwise thereto. After completion of the dropwise addition, the temperature of the reaction mixture was raised to −30° C., and a solution of 4-(4-(1,3-dioxolan-2-yl)cyclohexyl)cyclohexanone (5.0 g) in THF (50 ml) was added dropwise thereto. After completion of the dropwise addition, the temperature of the reaction mixture was raised to room temperature, followed by stirring for 18 hours. The reaction mixture was added in ice water, extracted with toluene, washed with water, and then dried over anhydrous magnesium sulfate. The solution was concentrated in vacuo and then subjected to isolation and purification by silica gel column chromatography, thereby obtaining a colorless crystal of 1-(8-fluoro-3,4-dihydrocoumarin-6-yl)-4-(4-(1,3-dioxolan-2-yl)cyclohexyl)cyclohexanol (4.5 g).

Provenance & Evidence