Tetrahydrofuran → HCID 86681444, compound

To a solution of 4-(methoxymethyl)-1-methyl-1H-pyrazole (261.0 mg, 2.069 mmol) in tetrahydrofuran (5 mL, 60 mmol) at 0° C. was added 1.6 M n-butyllithium in hexane (3.88 mL, 6.21 mmol). The solution was stirred at room temperature for 1 h and cooled to −78° C. To the solution was added 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.46 mL, 2.3 mmol). The reaction was stirred at −78° C. for 0.5 h and then warmed up to 0° C. (taking 0.5 h). The reaction mixture was quenched with brine, adjusted to pH=6-7 with 1 N HCl aqueous solution, and extracted with EtOAc (3×). The combined organic phases were washed with brine, dried over Na2SO4, and concentrated to give brown oil, which was purified by combi-flash chromatography. LC/MS found: 253.1 (M+1)+.

1. temperaturecooled to −78° C
2. stirringThe reaction was stirred at −78° C. for 0.5 h
3. temperaturewarmed up to 0° C. (taking 0.5 h)
4. customThe reaction mixture was quenched with brine
5. extractionextracted with EtOAc (3×)
6. washThe combined organic phases were washed with brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customto give brown oil, which
10. customwas purified by combi-flash chromatography

ORD record

ord-5a5d2463d2124121a4eeaa59773153ab

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895571B2