Ethyl isonicotinate → HCID 44239663, compound

Temperature

40 °C

H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added dropwise over 2 min to a stirred solution of ethyl isonicotinate 1d (151 mg, 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 40 °C. 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 40 °C 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 at 40 °C for 60 min, then diluted with EtOAc (50 mL). The mixture was poured in to saturated NaHCO3 (5 mL) and brine (100 mL). The aqueous and organic layers were partitioned and the organic layer was washed with brine (3 x 20 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by column chromatography on silica gel using EtOAc / hexanes (1:19 to 2:3) to give the desired product 2d (49 mg, 24%) as an oil.

ORD record

ord-2658d2fffcce43018f8455223d2c38f6

Source dataset

Minisci dataset from Roche

DOI

10.1021/jo9010624