2-Methylquinoline → HCID 44239661, compound

Temperature

25 °C

H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added dropwise over 1-2 min to a stirred solution of quinaldine 1b (135 μL, 1.0 mmol), concentrated H2SO4 (107 μL, 2.0 mmol), 3-iodooxetane (368 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at room temperature. After 1-2 min a further portion of iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added and the mixture was stirred at room temperature for 30 min. Further H2O2(0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred for 60 min, then poured into a 0.2 M solution of NaOH (30 mL) and Et2O (50 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with Et2O (2 x 25 mL). The combined organic extracts were washed with brine (1 x 30 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by preparative thin-layer chromatography using EtOAc / hexanes (3:7) as eluent to give recovered quinaldine 1b (55 mg, 39%), and the desired product 2b (64 mg, 32%) as a solid. An analytical portion of the product 2b was recrystallized from hexanes for data purposes.

ORD record

ord-fd67d32167634289bf001446bf234950

Source dataset

Minisci dataset from Roche

DOI

10.1021/jo9010624