反应详情

To a suspension of 2-fluorobenzeneamine (1 mL, 7.80 mmol) in DCM (78 mL) was added TMSCl (0.99 mL, 7.80 mmol) at RT [Rigo, B.; Fasseur, D.; Cauliez, P. and Couturier, D. Tetrahedron Lett.; 30; 23; 1989; 3073-3076.]. The reaction mixture was stirred for 30 min then 2,2-dimethyl-1,3-dioxane-4,6-dione (1.12 g, 7.80 mmol) was added and the combined mixture was stirred overnight. The solvent was removed under reduced pressure and the residue was dissolved in NaHCO3 solution, which was washed with EtOAc. The organic phase was discarded and the aqueous phase was acidified with conc. HCl to pH˜3, extracted with EtOAc; extract was dried (anhydrous Na2SO4) and concentrated. The residue was purified by flash chromatography (eluent CHCl3/MeOH/AcOH 8:1:0.1) to afford the acid 29 (0.4 g, 26% yield) as a white solid. 1H NMR (DMSO-d6) δ (ppm): 12.67 (s, broad, 1H), 9.95 (s, 1H), 7.95 (m, 1H), 7.25 (m, 1H), 7.12 (m, 1H), 3.43 (s, 2H). MS (m/z): 198.0 (M+H).

1. stirringthe combined mixture was stirred overnight
2. customThe solvent was removed under reduced pressure
3. dissolutionthe residue was dissolved in NaHCO3 solution
4. washwhich was washed with EtOAc
5. extractionextracted with EtOAc
6. extractionextract
7. dry with materialwas dried (anhydrous Na2SO4)
8. concentrationconcentrated
9. customThe residue was purified by flash chromatography (eluent CHCl3/MeOH/AcOH 8:1:0.1)