Potassium Phosphate, Tribasic → 2-[6-(3-Adamantan-1-yl-4-methoxyphenyl)-naphthalen-2-yl]-3-hydroxy-cyclopent-2-enone

Participants

Reaction Conditions

Reaction Steps

A flame-dried Schlenk tube containing a Teflon coated stir bar was charged with Pd(OAc)2 (20 mg, 0.088 mmol), (2-dicyclohexylphosphino)-2′,4′,6′-triisopropyl biphenyl (105 mg, 0.22 mmol), 1,3-cyclopentanedione (65 mg, 0.66 mmol), toluene-4-sulfonic acid 6-(3-adamantan-1-yl-4-methoxyphenyl)-naphthalen-2-yl ester (238 mg, 0.44 mmol) and finely ground K3PO4 (233 mg, 1.1 mmol). The tube was capped with a septum, evacuated and backfilled with nitrogen three times, 2 mL of dry dioxane was injected and the mixture was heated to 100° C. for 3 h. The mixture was then cooled, diluted with EtOAc, washed with 1N HCl, dried over Na2SO4 and filtered. The filtrate was concentrated and purified by flash chromatography using MeOH—CH2Cl2.

Provenance & Evidence