Sodium Methoxide → 5-(methoxymethyl)-1-methyl-3-nitro-1H-pyrazole

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 5-(bromomethyl)-1-methyl-3-nitro-1H-pyrazole (8.8 g, 40 mmol), sodium methoxide (4.3 g, 80 mmol), and methanol (50 mL). The reaction mixture was heated at reflux for 2 h. After this time the reaction was cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between ethyl acetate (60 mL) and water (60 mL). The aqueous layer was separated and extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with brine (50 mL) and dried over sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to afford 336a as a yellow oil (6.1 g, 90%). MS-ESI: [M+H]+ 172.

1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
2. temperatureThe reaction mixture was heated
3. temperatureat reflux for 2 h
4. concentrationconcentrated under reduced pressure
5. customThe residue was partitioned between ethyl acetate (60 mL) and water (60 mL)
6. customThe aqueous layer was separated
7. extractionextracted with ethyl acetate (2×50 mL)
8. washThe combined organic layer was washed with brine (50 mL)
9. dry with materialdried over sodium sulfate
10. customThe drying agent was removed by filtration
11. concentrationthe filtrate was concentrated under reduced pressure

ORD-Eintrag

ord-3fae23fb50004052af7f16bce9ea0c1a

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08921353B2