N,N,N',N'-Tetramethylethylenediamine → HCID 89962427, compound

Temperature

-78 °C

To a solution of 1-methylpyrazole (9.34 g, 114 mmol) and N,N,N′,N′-tetramethylethylenediamine (17.1 mL, 114 mmol) in THF (300 mL), butyl lithium (1.63 M solution in hexane; 81.7 mL, 133 mmol) was added at −78° C. The reaction solution was stirred at −78° C. for 30 minutes. Then, cyclohexene oxide (13.9 mL, 137 mmol) was added thereto, and the mixture was stirred at room temperature for 15 hours. To the reaction solution, water (1 L) was added, followed by extraction with ethyl acetate (500 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (ethyl acetate) to yield the title compound (11.2 g, 55%) as a colorless solid.

1. stirringthe mixture was stirred at room temperature for 15 hours
2. extractionfollowed by extraction with ethyl acetate (500 mL)
3. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
4. concentrationAfter vacuum concentration
5. customthe residue was purified with silica gel chromatography (ethyl acetate)

ORD record

ord-5b67503fb10b4938a1f099943c6e101a

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889741B2