3-Oxetanone → HCID 71272554, compound

Participants

Reaction Conditions

Reaction Steps

Into a 5 L 4-necked round-bottom flask under nitrogen was placed 3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazole (132.0 g, 452.89 mmol, 1.00 equiv.) in THF (2 L), followed by the addition of butyl lithium (208 mL, 2.4 M, 1.10 equiv) dropwise with stirring at −78° C. over 15 min. The resulting solution was stirred at −50° C. for 40 min. To this was added a solution of oxetan-3-one (40.0 g, 555.07 mmol, 1.20 equiv) in THF (500 mL), dropwise with stirring at −78° C. over 30 min. The resulting solution was stirred at −78° C. for 30 min then quenched by the addition of 2 L of satd. aq. NH4Cl. The mixture was concentrated in vacuo and extracted with 3×1 L of EtOAc. The combined organic layers were washed with 2×1 L of water and 1×500 mL of brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with EtOAc/petroleum ether (1:20-1:5) to afford 3-[3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazol-5-yl]oxetan-3-ol (142.0 g, 82% yield) as a light yellow oil.

Provenance & Evidence