acetic anhydride; hydrogenchloride; water;
reactants can be synthesized in 1 step.
gallaschun, randall, wo2014/143799, a2, (2014) step 2 (5-methylpyridin-2-yl)methanol 2, 5-dimethylpyridine 1 -oxide (2.5g, 20.3 mmol) was added to acetic anhydride (8.2ml) at 100 °c over a period of 30 min. then the mixture was refluxed 1 h. the m ixture was cooled to room temperature and carefully quenched with ethanol (1 lml). the reaction mixture was concentrated. the residue was treated with in hc1 (6 ml) and refluxed 1 h. the reaction was concentrated and the residue was partitioned between ethyl acetate and water. the organic phase was dried over sodium sulfate, filtered and concentrated to give (5-methylpyridin-2-yl) methanol (2g, 80 .0percent yield) as a light yellow oil. lcms mh 124.
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