Toluene → HCID 58460235, compound

Participants

Reaction Steps

Tetrabutylammonium bromide (785 mg) was added to a stirred mixture of Intermediate 17 (800 mg), 4-chlorobenzyl bromide (1101 mg) in sodium hydroxide 20% aq. (9 mL) and toluene (20 mL). The RM was stirred at room temp under nitrogen atm. for 1.5 hours. Sat. NH4Cl aq solution (50 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 using a cyclohexane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (467 mg). LC/MS MH+ 289, Rt 0.92 min (2 minute run).

Provenance & Evidence