Potassium Carbonate → (5-Chloro-6-ethyl-3-pyridinyl)methanol

To a solution of (5,6-dichloro-3-pyridinyl)methanol (500 mg, 2.81 mmol), K2CO3 (1165 mg, 8.43 mmol), and [1,1′-Bis(diphenylphosphino) ferrocene]dichloro-palladium(II) (206 mg, 0.281 mmol) in THF (17 ml), was added diethylzinc (5.67 ml, 5.67 mmol). The mixture was stirred under reflux for 16 h in a pressure tube. The resulting mixture was quenched upon the addition of aqueous HCl until pH 7 and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by flash chromatography using Flashmaster II, spherical silica gel cartridge BP-SUP 20-40μ, and mixtures of EtOAc and hexane as eluents to give 103 mg of desired compound.

1. temperatureunder reflux for 16 h in a pressure tube
2. customThe resulting mixture was quenched upon the addition of aqueous HCl until pH 7
3. extractionextracted with EtOAc
4. washThe combined organic layers were washed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by flash chromatography

ORD record

ord-c4da075870714262a2c6c1bd8bfc9dee

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08097628B2