Hydrogen Peroxide → HCID 131716835, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3.21 g of the oxazolidone 15 in 40 ml of methylene chloride at -78° C. was added 13.64 ml of a 1M dibutylboron triflate in methylene chloride solution and 2.6 ml of triethylamine. The reaction solution was stirred at 0° C. for 30 minutes, then it was cooled to -78° C. 3-(4-Methoxybenzyloxy)propanaldehyde (2.4 g) in 4 ml of methylene chloride was added and the reaction solution was stirred 30 minutes at -78° C. and then at RT for 1.5 hour. At the end of this time 100 ml of pH7 phosphate buffer was added, followed by addition of 30% aqueous hydrogen peroxide to the mixture at 0° C. The mixture was then extracted twice with diethyl ether and the aqueous phases were dried with sodium sulfate. The solution was concentrated under vacuum and chromatography of the residue over silica gel (2 hexanes: 1 EtOAc) provided the title compound.

Provenance & Evidence