Ethylene Glycol → HCID 58923385, compound

Participants

Reaction Steps

A solution of 6-fluoro-1-hydroxy-3-morpholin-4-yl-xanthen-9-one (30.0 mg, 0.095 mmol) and ethylene glycol (59.1 mg, 0.951 mmol) in anhydrous DMF (1 mL) was treated with NaH (40.0 mg, 0.951 mmol). The bubbling reaction was stirred for 15 minutes at room temperature, then heated at 80° C. for 1 hour. The reaction mixture was quenched with water and extracted with EtOAc (3×50 mL). The combined organics were washed with water (3×15 mL), dried (MgSO4), and concentrated to produce an oil. The oil was purified via Biotage chromatography using a gradient of 2.5%-5% MeOH/CH2Cl2 as eluent to yield 12 mg (35%) of 1-hydroxy-6-(2-hydroxyethoxy)-3-morpholin-4-yl-xanthen-9-one as a white powder. Rf=0.55 (5% MeOH/CH2Cl2). 1H NMR (DMSO-d6, 400 MHz) δ: 12.91 (s, 1H), 8.05 (d, 1H), 7.10 (m, 2H), 6.48 (s, 1H), 6.34 (s, 1H), 4.98 (m, 1H), 4.18 (t, 2H), 3.78 (t, 2H), 3.70 (m, 4H), 3.38 (m, 4H). LRMS (APCI, positive): Da/e 358.4 (m+1).

Provenance & Evidence