Morpholine → HCID 58805171, compound

Participants

Reaction Steps

A solution of trifluoromethanesulfonic acid 4-acetyl-3,5-dihydroxy-phenyl ester (1.0 g, 3.33 mmol), morpholine (0.35 mL, 3.99 mmol), tris(dibenzylideneacetone) dipalladium(0) (153 mg, 0.167 mmol), biphenyl-2-yl-di-tert-butyl-phosphane (198 mg, 0.666 mmol), and K3PO4 (1.41 mg, 6.66 mmol) in THF (2 mL) was heated to 85° C. in a sealed tube for 2 h. The reaction mixture was allowed to cool to room temperature, and filtered through a ¾″ silica gel (60 Å) plug. The plug was washed with EtOAc (75 mL) and the filtrate concentrated. The concentrate was purified via Biotage chromatography with gradient elution from 100% hexanes to 40% EtOAc/hexanes to yield 475 mg (60%) of 1-(2,6-dihydroxy-4-morpholin-4-yl-phenyl)-ethanone. Rf=0.16 (50% EtOAc/hexanes).

Provenance & Evidence