反应详情

To a solution of 2-bromo-4-methylpyridine (600 mg) in diethyl ether (20 mL) at −78° C. is added a 2.3M solution of butyllithium in hexanes (1.52 mL). After stirring at this temperature for 1 hour 2-fluoro-4-methylbenzaldehyde is added and the mixture allowed to warm at room temperature. The reaction mixture is then hydrolyzed with diluted aqueous hydrochloric acid, washed with diethyl ether, basified with concentrated sodium hydroxide and extracted with diethyl ether. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography over silica gel (heptane/ethyl acetate 2/1) to afford (2-fluoro-4-methylphenyl)(4-methyl-pyridin-2-yl)methanol as a pale yellow oil which solidifies on standing.

1. additionis added
2. washhydrolyzed with diluted aqueous hydrochloric acid, washed with diethyl ether
3. extractionextracted with diethyl ether
4. dry with materialThe pooled organic extracts are dried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue is purified by chromatography over silica gel (heptane/ethyl acetate 2/1)