Tetrahydrofuran → HCID 66783589, compound

Participants

Reaction Steps

To a sol. of 4-but-3-enylthiazole (2.07 g, 14.9 mmol) in THF (20 mL), tBuOH (10 mL) and water (5 mL), was added NMO (2.21 g, 16.4 mmol). OsO4 (2.5 wt % in tBuOH, 3.74 mL, 0.298 mmol) was added. The sol. was stirred for 3 h. A sol. of Na2SO3 (1.5 g) in 20 mL water was added. Brine (200 mL) was added and this mixture was extracted with EtOAc (4×). The combined org. phases were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 3:7→1:1→3:1→EtOAc→MeOH/EtOAc 1:9) yielded the title compound (1.63 g, 63%).

Provenance & Evidence