Benzaldehyde → HCID 68810852, compound

Temperature

0 °C

n-Butylmagnesium chloride (3.49 mmol) in 2.05M tetrahydrofuran solution (1.70 mL) was added to ice-cooled n-butyllithium (6.99 mmol) in 1.52M hexane (4.60 mL). The mixture was stirred at 0° C. for 15 minutes to give a suspension. The suspension was added to a tetrahydrofuran solution (25 mL) containing 3,5-dibromopyridine (2.37 g, 10.0 mmol) over a period of 10 minutes or more, while keeping the temperature below −5° C., to give an orange suspension. The suspension was stirred at −10° C. for one hour, and benzaldehyde (1.35 mL, 13.3 mmol) was added thereto. The resultant mixture was stirred at 0° C. for 30 minutes, and then 1M acetic acid solution (15 mL) was added. The reaction mixture was extracted twice with ethyl acetate (20 mL). The organic extracts were combined, washed with saturated aqueous sodium chloride (10 mL), dried over magnesium sulfate and was purified by flash column chromatography on silica gel in a developing solvent system of hexane-ethyl acetate (5:1, v/v) to give the title compound (1.647 g, 59% yield) as a colorless oil.

1. customto give a suspension
2. customthe temperature below −5° C.
3. customto give an orange suspension
4. stirringThe suspension was stirred at −10° C. for one hour
5. extractionThe reaction mixture was extracted twice with ethyl acetate (20 mL)
6. washwashed with saturated aqueous sodium chloride (10 mL)
7. dry with materialdried over magnesium sulfate
8. customwas purified by flash column chromatography on silica gel in a developing solvent system of hexane-ethyl acetate (5:1

ORD record

ord-fbc1c8f235074e859453ec15d3657d15

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439535B2