(S)-(+)-3-Hydroxytetrahydrofuran → (2-Chloro-5-iodophenyl)(4-(((3S)-tetrahydro-3-furanyl)oxy)phenyl)methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 60.56 g (2-chloro-5-iodo-phenyl)-(4-fluoro-phenyl)-methanone in 170 mL of tetrahydrofuran and 16.46 g of (S)-3-hydroxytetrahydrofuran is added 26 g of potassium tert-butoxide in 250 mL of tetrahydrofuran at 0 to 5° C. The solution is stirred at 10° C. for 0.5 hour. The reaction is quenched with 170 mL of water and 170 mL of methyl tert-butyl ether at 0 to 25° C. The product is washed with 170 mL of brine (3 weight-%). The solvent is removed upon evaporation and crystallized in 220 mL of iso-propylacetate.

Provenance & Evidence