4-Pyridinecarboxaldehyde → alpha-Methyl-4-pyridinemethanol

4-Pyridinecarbaldehyde (1.00 ml, 10.5 mmol) in tetrahydrofuran (10 mL) was mixed with methylmagnesium bromide (0.97 M in tetrahydrofuran, 19.5 mL, 18.9 mmol) under cooling with ice and stirred at room temperature for 5 hours. After quenching by adding water under cooling with ice, the reaction solution was mixed with ethyl acetate, and the organic layer was washed with saturated aqueous ammonium chloride, dried over anhydrous sodium sulfate and evaporated under reduced pressure to give the desired product (283 mg, 22% yield).

1. temperatureunder cooling with ice
2. customAfter quenching
3. additionby adding water
4. temperatureunder cooling with ice
5. additionthe reaction solution was mixed with ethyl acetate
6. washthe organic layer was washed with saturated aqueous ammonium chloride
7. dry with materialdried over anhydrous sodium sulfate
8. customevaporated under reduced pressure

ORD record

ord-3e7a6259f90b4305ad606cd0c2171da4

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08440666B2