Tetrabutylammonium Fluoride → HCID 71272738, compound

Temperature

88 °C

Into a 250-mL round-bottom flask under nitrogen was placed 3-(2,5-dimethyl-1H-pyrrol-1-yl)-5-(oxetan-3-yl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazole (12.0 g, 34.5 mmol, 1.0 equiv.), followed by the addition of a solution of TBAF (120 g, 5.0 equiv) in THF (120 mL). The resulting solution was stirred at 88° C. for 8 h, cooled to 30° C., concentrated in vacuo and diluted with 200 mL of EtOAc. The resulting mixture was washed with 2×300 mL of water and 2×100 mL of brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with EtOAc/PE (1:100-1:3) to afford 3-(2,5-dimethyl-1H-pyrrol-1-yl)-5-(oxetan-3-yl)-1H-pyrazole (4.0 g, 48% yield) as a white solid.

1. customInto a 250-mL round-bottom flask under nitrogen was placed
2. temperaturecooled to 30° C.
3. concentrationconcentrated in vacuo
4. additiondiluted with 200 mL of EtOAc
5. washThe resulting mixture was washed with 2×300 mL of water and 2×100 mL of brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customThe residue was purified by SiO2 chromatography
9. washeluting with EtOAc/PE (1:100-1:3)

ORD record

ord-a3c6f4000f8a4c2fad9bee0a717fcf09

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637537B2