Hydrogen Peroxide → HCID 131716835, compound

Temperature

0 °C

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.

1. temperatureit was cooled to -78° C
2. stirringthe reaction solution was stirred 30 minutes at -78° C.
3. waitat RT for 1.5 hour
4. extractionThe mixture was then extracted twice with diethyl ether
5. dry with materialthe aqueous phases were dried with sodium sulfate
6. concentrationThe solution was concentrated under vacuum and chromatography of the residue over silica gel (2 hexanes: 1 EtOAc)

ORD record

ord-4d13c309a9c844378dcbee9b1c0f0daf

Source dataset

uspto-grants-1991_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05011943