Toluene → HCID 19755396, compound

Participants

Reaction Steps

To 454 mg (1 mmol) of ester from Step 5 in THF (15 ml) at -78° C. is added lithium hexamethyldisilazide in toluene (1.1 mmol), followed by hexamethylphosphoramide (1.5 ml). After 15 minutes, p-chlorobenzyl bromide (300 mg) is added and the reaction is allowed to warm to room temperature. The reaction mixture is then poured into 5% aqueous NH4Cl, extracted with 2×100 ml Et2O and the organic extracts dried over MgSO4. Filtration and evaporation of the solvent left a crude residue, which, after chromatography over silica using EtOAc-hexane, yields ethyl 9-p-chlorobenzyl-6-(quinolin-2-ylmethoxy)-5-allyl-1,2,3,4-tetrahydrocarbazol-1-ylacetate.

Provenance & Evidence