Phosphorus oxychloride → HCID 86679023, compound

Participants

Reaction Conditions

Reaction Steps

Phosphoryl chloride (1.428 mL, 15.36 mmol) was added to a stirred solution of the intermediate from Step D (0.6534 g, 1.920 mmol) in dry ClCH2CH2Cl (14.44 mL). The resulting solution was heated at 120° C. overnight. Another 8 eq. POCl3 was added and the reaction was heated at 120° C. for 2 days. The reaction was cooled to room temperature and concentrated in vacuo. The reaction was diluted with water and EtOAc and basified by the careful addition of saturated aq. NaHCO3 until not further effervescence was observed. The layers were separated and the aqueous layer was further extracted with EtOAc (2×). The organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by silica gel chromatography using a hexanes/EtOAc gradient to afford the desired product, as a colorless solid. 1H NMR (500 MHz, CHCl3-d) δ 9.31 (d, J=7.2 Hz, 1H); 7.59 (d, J=9.1 Hz, 1H); 7.08 (dd, J=9.0, 6.6 Hz, 1H); 6.96-6.90 (m, 1H); 4.03 (s, 3H); 3.25-3.19 (m, 2H); 2.66-2.52 (m, 2H). m/z=323.0 (M+H).

Provenance & Evidence