Phosphorus oxychloride → HCID 87741012, compound

Participants

Reaction Steps

A mixture of Example 29C (0.63 g, 2.7 mmol) and phosphorus oxychloride (10 mL) was heated at reflux for 1 hour, cooled, concentrated under reduced pressure followed by the addition of water (20 mL). The mixture was filtered and the resulting solid was taken up in 1 M HCl (20 mL) and heated at reflux for 5 minutes. The cooled mixture was basified with 1M NaOH and extracted with CH2Cl2 (3×), filtering each extraction through diatomaceous earth. The combined CH2Cl2 layers were dried (MgSO4), filtered, concentrated under reduced pressure and chromatographed on silica gel eluting with a gradient of CH2Cl2:EtOAc (20:1 and 10:1) to provide the title compound. 1H NMR (CDCl3) δ 2.94 (t, J=6.10 Hz, 2H), 4.52 (t, J=6.27 Hz, 2H), 5.15 (s, 2H), 7.13 (dd, J=7.97, 1.19 Hz, 1H), 7.21-7.30 (m, 1H), 7.41-7.49 (m, 1H), 7.82 (dd, J=7.80, 1.70 Hz, 1H); MS (M+H)+ m/z 248.

Provenance & Evidence