反应详情

温度

59 °C

A well-stirred solution of (25) (0.295 g., 1.0 mM), methyl iodide (0.25 mL, 4.0 mM) and anhydrous acetone (5.0 ml) is set in an oil-bath previously heated to 59° C., and kept for 2 minutes. Powdered anhydrous potassium hydroxide (0.225 g., 4.0 mM) is added all at once, and the bath temperature allowed to rise to 65° C. Clumping-up of some of the KOH is observed. After 15 additional minutes, the reaction mixture is removed from the bath, allowed to cool, and the volatiles removed. Methanol (7 mL) is added with stirring to the residue of N-Methyl-N-trifluoroacetyl-2-benzyloxyaniline (26) obtained, followed by water (1 mL), and methanol (2 mL) (to wash down the sides). After stirring overnight at ambient temperatures, the methanol is removed in vacuo, the residue distributed between ether and water, separated, the organic layer washed with additional water, saturated sodium chloride solution, and dried over sodium sulfate. Concentration of the filtered ether solution gives the title compound (27) (0.212 g.) as an oil. NMR, MS, and TLC indicate little, if any, dimethyl compound.

1. customto rise to 65° C
2. customAfter 15 additional minutes, the reaction mixture is removed from the bath
3. temperatureto cool
4. customthe volatiles removed
5. additionMethanol (7 mL) is added
6. customobtained
7. washto wash down the sides)
8. stirringAfter stirring overnight at ambient temperatures
9. customthe methanol is removed in vacuo
10. customseparated
11. washthe organic layer washed with additional water, saturated sodium chloride solution
12. dry with materialdried over sodium sulfate