反应详情

To methyl 3-(hydroxymethyl)-5-methylbenzoate prepared by the method in EXAMPLE SP-198, Step 2 in anhydrous methylene chloride at −30° C. is added methanesulfonyl chloride (601 μL, 7.8 mmol), then triethylamine (1.5 mL, 11.1 mmol), and the reaction is stirred at 0° C. 15 min. The resulting precipitate is filtered, and the filtrate is added to N-methylisoamylamine (2.1 mL, 16.7 mmol). The reaction stirred at room temperature 16 h. The solution is concentrated under reduced pressure, redissolved in ethyl acetate and washed with saturated sodium bicarbonate, brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 20% ethyl acetate/hexanes) provides the title compound. ESI MS m/z 264.2 [M+H]+.

1. custom15 min
2. filtrationThe resulting precipitate is filtered
3. concentrationThe solution is concentrated under reduced pressure
4. dissolutionredissolved in ethyl acetate
5. washwashed with saturated sodium bicarbonate, brine
6. dry with materialdried (sodium sulfate)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customPurification by flash column chromatography (silica, 20% ethyl acetate/hexanes)