Acetonitrile → HCID 72269293, compound

Participants

Reaction Steps

In argon atmosphere, 6,8,10-undecatrien-3-ol (5) (1.80 g, 10.8 mmol), methylene chloride (45 mL), Molecular Sieves 4A (4.50 g), N-methylmorpholine N-oxide (NMO) (1.90 g, 16.2 mmol) and acetonitrile (5 mL) were added to a 100 mL flask, and further tetrapropylammonium perruthenate (TPAP) (190 mg, 0.541 mmol) was added, followed by stirring at room temperature for 4 h. TPAP (190 mg, 0.541 mmol) was added, followed by stirring for 2 h at room temperature. Then NMO (1.90 g, 16.2 mmol) was added, followed by stirring for 3 h at room temperature. Hexane was added to the reaction mixture which then was filtered, and the filtrate was concentrated under reduced pressure. Thus obtained residue was purified on silica gel column chromatography (hexane:ethyl acetate=50:1) to give 6,8,10-undecatrien-3-one (1-1) (476 mg, 2.90 mmol, yield 27%).

Provenance & Evidence