Toluene → HCID 58460143, compound

Participants

Reaction Steps

Tetrabutylammonium bromide (317 mg) was added to a stirred mixture of Intermediate 32 (350 mg), 4-chlorobenzyl bromide (444 mg) in sodium hydroxide 15% aq. (10 mL) and toluene (15 mL). The RM was stirred at room temp under nitrogen atm. for 16 hours. Sat. NH4Cl aq. solution (10 mL) was added and the mixture was extracted with EtOAc (2×50 ml). The organics were combined, dried (hydrophobic frit) and concentrated under vacuum The residue was purified on silica (50 g) using a cyclohexane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (421 mg). LC/MS MH+ 303, Rt 2.51 min (5 minute run).

Provenance & Evidence