Hexane → HCID 69967781, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of (ethyl)triphenylphosphonium bromide (63.3 g, 170.5 mmol) in 270 mL of dry THF under Ar at 20° C., was added 91 mL of 1.8M phenyllithium in 70% cyclohexane/Et2O solution (163 mmol). After 30 minutes the reaction was cooled to -78° C., and a solution of 4-phenylmethoxy-3-nitrobenzaldehyde (38.96 g, 151.6 mmol) in 138 mL of THF was added by cannula over 25 minutes. The reaction was maintained at -78° C. for 60 minutes and stirred at 20° C. overnight prior to addition of 400 mL hexane. The supernatant was decanted and the solids stirred twice with additional THF/hexane which was also decanted. After concentration of the combined supernatants, the title compound (11.33 g, 1:1 trans to cis ratio) was eluted from silica gel by 0% to 25% EtOAc/hexane.

Provenance & Evidence