Iodine → HCID 59379098, compound

Participants

Reaction Conditions

Reaction Steps

Into a clean flame dried and Ar flushed 500 mL RBF was added 14.2 mL (65 mmol) of commercially available 24. To this mixture was added 100 mL of anhydrous THF, 1.9 g (78 mmol) of Mg turnings and a pellet of I2 to accelerate the reaction. The reaction mixture was refluxed for 2 h and then cooled to room temperature and further to −78° C. To this was added 7.0 g (20.0 mmol) of 21 in 20 mL of anhydrous THF followed by addition of 6.5 mL (0.65 mmol) of lithium cuprate. The resulting mixture was allowed to warm to room temperature while stirring overnight followed by quenching with saturated aq. NH4Cl and extracted with EtOAc (3×). The combined EtOAc layers were then successively washed with water, saturated aq. NaHCO3 and brine, dried over MgSO4 and the solvents evaporated under reduced pressure. The residue was then purified by combiflash using hexane/EtOAc as eluent to furnish 6.3 g of the compound 27 as colorless oil in 95% yield.

Provenance & Evidence