Methyl morpholine oxide → Ethyl 1-(p-chlorophenyl)-beta-oxocyclopropanepropionate

Participants

Reaction Steps

A solution of ethyl 1-(p-chlorophenyl)-β-hydroxy-cyclopropanepropionate (7.9 g, 29.4 mmol) and 4-methyl-morpholine N-oxide (14.0 g, 120 mmol) in acetonitrile containing 30 4 Å molecular sieves is stirred at room temperature for 20 minutes, treated with tetrapropyl-ammonium perruthenate (0.8 g, 2.3 mmol), stirred for two hours while maintaining the reaction mixture temperature at room temperature with an ice-water bath, diluted with diethyl ether, filtered through diatomaceous earth, and concentrated in vacuo to obtain a residue. A solution of the residue in diethyl ether is washed sequentially with water, 5% sulfuric acid, water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a dark oil. Chromatography of the oil using silica gel and a 1:19 to 3:17 ethyl acetate/hexanes gradient gives the title product as a pale yellow oil (4.3 g, 55%) which is identified by NMR spectral analyses.

Provenance & Evidence