Methanol → HCID 54202767, compound

Participants

Reaction Conditions

Reaction Steps

10.00 g (25.6 mmole) of 1-azido-4-t-butyldimethylsilyloxy-(2R)-(3,4-dichlorophenyl)-2-butanol [prepared as described in step (d) above] were dissolved in 100 ml of tetrahydrofuran and 0.6 ml of water, and 7.39 g (28.2 mmole) of triphenylphosphine were added to the resulting solution. The mixture was then stirred under a nitrogen atmosphere at 80° C. for 4 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, hexane was added to the resulting residue and the deposited crystals were removed by filtration. The filtrate was concentrated by evaporation under reduced pressure, and the resulting residue was purified by silica gel flash column chromatography, using a gradient elution method, with mixtures of methylene chloride and methanol ranging from 30:1 to 10:1 by volume as the eluent, to obtain 3.83 g (yield 41%) of the title compound as a colorless oil.

Provenance & Evidence