Sodium hydride → HCID 58405813, compound

Temperature

0 °C

Into a 3 L 4-necked round-bottom flask under nitrogen was placed a solution of 3-nitro-1H-pyrazole (100 g, 884.37 mmol, 1.00 equiv.) in THF (1.5 L), followed by the addition of NaH (53 g, 1.32 mol, 1.50 equiv, 60% suspension) batchwise at 0° C. The resulting solution was stirred at 0° C. for 1 h. A solution of [2-(chloromethoxy)ethyl]trimethylsilane (117.4 g, 704.17 mmol, 1.20 equiv) in THF (500 mL) was then added dropwise with stirring at 0° C. The resulting solution was stirred at 25° C. for 1 h, quenched by the addition of EtOH (200 mL), concentrated under vacuum and diluted with 2 L of EtOAc. The resulting mixture was washed with 2×1 L of brine, dried (Na2SO4) and concentrated in vacuo. The residue was triturated with 200 mL of petroleum ether. The solids were collected by filtration and washed with petroleum ether (2×500 mL) to afford 125 g (52%) of 3-nitro-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazole as a yellow solid.

1. customInto a 3 L 4-necked round-bottom flask under nitrogen was placed
2. stirringwith stirring at 0° C
3. stirringThe resulting solution was stirred at 25° C. for 1 h
4. customquenched by the addition of EtOH (200 mL)
5. concentrationconcentrated under vacuum
6. additiondiluted with 2 L of EtOAc
7. washThe resulting mixture was washed with 2×1 L of brine
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated in vacuo
10. customThe residue was triturated with 200 mL of petroleum ether
11. filtrationThe solids were collected by filtration
12. washwashed with petroleum ether (2×500 mL)

ORD record

ord-b459c71c2f3a48b3befb5c1830ee1b40

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637537B2