Phosphorus oxychloride → HCID 117739138, compound

Participants

Reaction Conditions

Reaction Steps

To Intermediate 3E (8.8 g, 36.0 mmol) was added phosphoryl trichloride (59.3 mL, 648 mmol). The suspension was heated at 115° C. for 1.0 h. Solvent was removed under high vacuum. The residue was diluted with EtOAc, washed with sat. sodium bicarbonate, brine and dried over sodium sulfate. After evaporation of solvent, the crude product was dissolved in a small amount of chloroform and charged to a 120 g silica gel cartridge which was eluted with 2% EtOAc in hexanes for 6 min, then a 15 min gradient from 2% to 25% EtOAc in hexanes. The desired fractions were combined and concentrated to give Intermediate 3F (8.5 g, 37.5 mmol, 104% yield) as a slightly yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 9.01 (s, 1H) 8.46-8.56 (m, 2H) 8.34 (s, 1H); 19F NMR (376 MHz, chloroform-d) δ ppm −136.54 (s, 1F); MS (ESI) m/z: (M+H)+ 227.1.

Provenance & Evidence