1-Methoxyphthalazine → HCID 44239509, compound

Temperature

60 °C

H2O2 (30% in H2O; 0.23 mL, 2.25 mmol) was added dropwise over 5 min to a stirred solution of 1-methoxyphthalazine 1l (120 mg, 0.75 mmol), concentrated H2SO4 (80 μL, 1.5 mmol), 3-iodooxetane (276 mg, 1.5 mmol) and iron(II) sulfate heptahydrate (63 mg, 0.225 mmol) in DMSO (7.5 mL) at 60 °C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (50 mg, 0.19 mmol) was added and the mixture was stirred at 60 °C for 60 min. Ater allowing to cool, the mixture was poured into a 0.2 M solution of NaOH which has been saturated with solid NaCl (40 mL) and EtOAc (50 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with EtOAc (1 x 30 mL). The combined organic extracts were dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using EtOAc / hexanes (0:1 to 3:2) to give the desired product 2l (54 mg, 34%) as a solid. An analytical sample was triturated with Et2O / EtOAc for data purposes.

ORD record

ord-3b08d7848aae4d6da08ad8bfcd983910

Source dataset

Minisci dataset from Roche

DOI

10.1021/jo9010624