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With potassium fluoride; tetrabutylammomium bromide In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere
General procedure: To a solution of the corresponding 1-alkyl-2H-3,1-benzoxazine-2,4(1H)-dione (N-alkylisatoic anhydride) 1a–d (10 mmol), KF (174 mg, 3 mmol) and TBAB (967 mg, 3 mmol) in dry DMF (20 ml) was added trimethyl(trifluoromethyl)silane (1.85 g, 13 mmol) dropwise at 0 8C under argon. After completion of addition, the reaction mixture was allowed to warm to rt and stirred for 5 h. The reaction was quenched with 5percent aq HCl solution (10 ml) at 0 8C, allowed to warm to rt, and stirred for 0.5 h. To the reaction mixture was added 10percent aq Na2CO3 solution (50 ml) with vigorous stirring, and stirring was continued for 1 h at rt. The resulting emulsion was extracted with hexanes (60 ml 3). The organic layer was separated, washed with brine (30 ml 2), dried over anhydrous MgSO4, and concentrated under reduced pressure.
Reference：
[1] Journal of Fluorine Chemistry, 2012, vol. 143, p. 272 - 280,9
2
[ 10328-92-4 ]
[ 81290-20-2 ]
[ 202270-41-5 ]
Yield
Reaction Conditions
Operation in experiment
61%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 20 h; Inert atmosphere
To a solution of 1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione 1a (0.61 g, 3.45 mmol) and trimethyl(trifluoromethyl)silane (638 mg, 4.49 mmol) in dry THF (15 ml) was added TBAF (1M in THF; 0.52 ml, 0.52 mmol) dropwise at 0 8C under argon. After completion of addition, the reaction mixture was allowed to warm to rt and stirred for 24 h. The reaction was quenched with 5percent aq HCl solution (10 ml) at 0 8C, allowed to warm to rt, and stirred 0.5 h.To the reaction mixture was added 10percent aq Na2CO3 solution (50 ml) under vigorous stirring, and stirring was continued for 1 h at rt. The resulting solution was extracted with hexanes (60 ml 3). The organic layer was washed with brine (30 ml 2), dried over anhydrous MgSO4, and concentrated under reduced pressure
Reference：
[1] Journal of Fluorine Chemistry, 2012, vol. 143, p. 272 - 280,9
With potassium fluoride; tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;
General procedure: To a solution of the corresponding 1-alkyl-2H-3,1-benzoxazine-2,4(1H)-dione (N-alkylisatoic anhydride) 1a-d (10 mmol), KF (174 mg, 3 mmol) and TBAB (967 mg, 3 mmol) in dry DMF (20 ml) was added trimethyl(trifluoromethyl)silane (1.85 g, 13 mmol) dropwise at 0 8C under argon. After completion of addition, the reaction mixture was allowed to warm to rt and stirred for 5 h. The reaction was quenched with 5% aq HCl solution (10 ml) at 0 8C, allowed to warm to rt, and stirred for 0.5 h. To the reaction mixture was added 10% aq Na2CO3 solution (50 ml) with vigorous stirring, and stirring was continued for 1 h at rt. The resulting emulsion was extracted with hexanes (60 ml 3). The organic layer was separated, washed with brine (30 ml 2), dried over anhydrous MgSO4, and concentrated under reduced pressure.
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20℃; for 20.0h;Inert atmosphere;
To a solution of 1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione 1a (0.61 g, 3.45 mmol) and trimethyl(trifluoromethyl)silane (638 mg, 4.49 mmol) in dry THF (15 ml) was added TBAF (1M in THF; 0.52 ml, 0.52 mmol) dropwise at 0 8C under argon. After completion of addition, the reaction mixture was allowed to warm to rt and stirred for 24 h. The reaction was quenched with 5% aq HCl solution (10 ml) at 0 8C, allowed to warm to rt, and stirred 0.5 h.To the reaction mixture was added 10% aq Na2CO3 solution (50 ml) under vigorous stirring, and stirring was continued for 1 h at rt. The resulting solution was extracted with hexanes (60 ml 3). The organic layer was washed with brine (30 ml 2), dried over anhydrous MgSO4, and concentrated under reduced pressure
With potassium fluoride; tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 0 - 20℃; for 20.0h;Inert atmosphere;
To a solution of compound 2a (0.36 g, 1.77 mmol), KF (30 mg, 0.52 mmol) and TBAB (168 mg, 0.52 mmol) in dry DMF (4 ml) was added trimethyl(trifluoromethyl)silane (0.71 g, 5.00 mmol) dropwise at 0 8C under argon. After completion of addition, the reaction mixture was allowed to warm to rt and stirred for 20 h. The reaction was quenched with 10% aq HCl solution (10 ml) at 0 8C, allowed to warm to rt, and stirred 2 h. The resulting solution was extracted with EtOAc (15 ml 3). The organic layer was washed with brine (15 ml 2), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purifiedby preparative TLC on silica gel (toluene/hexanes/EtOAc = 2:1:1) to afford compound 3a (266 mg, 55% yield) as a yellowish powder.
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