反应详情

To a mixture of paraformaldehyde (0.13 mol, 9 eq), 4 ml (1.5 eq) of triethylamine in 40 ml of 1,4-dioxane, 3-nitro-1-(4-octylphenyl)propyl acetate (13) (5 g, 0.015 mol) in 50 ml of 1,4-dioxane was added dropwise with stirring at RT, the mixture was slowly heated to 70° C., and stirred for 24 h at this temperature, under TLC control. To the reaction mixture was added water and the mixture, pH adjusted to ˜9-10 and stirred 16 h at 40° C. for deprotection (TLC and HPLC monitoring). After reaction completion (˜2-3 h) the mixture was extracted with ethyl acetate and washed successively with 1 N HCl, sodium bicarbonate solution and brine. The ethyl acetate solution was dried over sodium sulfate and concentrated. The residue was pure enough for transformation to the next step or can be purified by crystallization or silica gel column chromatography using hexane-ethyl acetate as eluent to afford a white solid with mp. 80-82° C., ESIMS 376.2 [M+Na]+

1. additionwas added dropwise
2. temperaturethe mixture was slowly heated to 70° C.
3. stirringstirred for 24 h at this temperature, under TLC control
4. stirringstirred 16 h at 40° C. for deprotection (TLC and HPLC monitoring)
5. customAfter reaction completion (˜2-3 h) the mixture
6. extractionwas extracted with ethyl acetate
7. washwashed successively with 1 N HCl, sodium bicarbonate solution and brine
8. dry with materialThe ethyl acetate solution was dried over sodium sulfate
9. concentrationconcentrated
10. customcan be purified by crystallization or silica gel column chromatography
11. customto afford a white solid with mp. 80-82° C., ESIMS 376.2 [M+Na]+