2-Fluoro-5-formylpyridine → 1-(6-Fluoropyridin-3-yl)ethan-1-ol

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Reaction Steps

Add methylmagnesium bromide (3 M in ether, 12 mL, 36 mmol) at 0° C. under nitrogen to a solution of 6-fluoro-pyridine-3-carbaldehyde (3 g, 24 mmol) in THF (20 mL). Continue to stir the mixture overnight at RT. Quench the mixture with 1 N HCl, followed by basification with diluted ammonium hydroxide to ˜pH 9. Extract the product with chloroform/IPA (3/1). Dry over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (10% methanol in DCM) to give the title compound as a colorless oil (2.3 g, 68%). MS (ES) m/z 142 [M+1]+.

Provenance & Evidence