Water → HCID 21964058, compound

Temperature

90 °C

Under an argon atmosphere, sodium (750 mg, 31.75 mmol) was added to refluxing cyclohexanol (15 mL). The mixture was refluxed until complete consumption of sodium. The remaining cyclohexanol was removed by a stream of argon to give a white solid, which was dissolved in N-methyl-pyrrolidinone (16 mL). After addition of 3,5-dibromopyridine (3 g, 12.66 mmol), the mixture was stirred and heated at 90° C. for 1 h, then cooled to room temperature, poured into cold (5° C.) water (60 mL), and extracted with diethyl ether (3×50 mL). The combined organic phases were washed with water (25 mL) and then brine (25 mL), then dried (MgSO4), filtered and concentrated by rotary evaporation to give 6.2 g of an orange oil, which was purified by column chromatography, eluting with cyclohexane/ethyl acetate (95/5, v/v). Selected fractions containing the product were concentrated via rotary evaporation to give 1.6 g (50%) of a light-yellow oil.

1. customThe remaining cyclohexanol was removed by a stream of argon
2. customto give a white solid, which
3. temperaturecooled to room temperature
4. extractionextracted with diethyl ether (3×50 mL)
5. washThe combined organic phases were washed with water (25 mL)
6. dry with materialbrine (25 mL), then dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated by rotary evaporation

ORD record

ord-9977cdde8039451ab5f9466805ca0b25

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07101896B2