3,6-Dimethoxypyridazine → HCID 44239664, 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 3,6-dimethoxypyridazine 1e (100 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 0.1 M solution of NaOH (30 mL) and EtOAc (30 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 (Na2SO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by column chromatography on silica gel to give the desired product 2e (33 mg, 22%) as a solid

ORD record

ord-a3a62c7a1bce45b2814d4ba02fbb278b

Source dataset

Minisci dataset from Roche

DOI

10.1021/jo9010624