Reaktion #595744
ord-6ff6ce2bf533459a8b3b3aa9dee2d208
Reaktionsgleichung
Edukte
Reagenzien
Reaktionsbedingungen
Aufarbeitung
- 1SonstigeA microwave vial equipped with a magnetic stir bar
Vorschrift
A microwave vial equipped with a magnetic stir bar was charged with 4-amino-6-(tert-butyl)-3-chloro-5-fluoropicolinaldehyde (316 mg, 1.370 mmol) and t-butanol (6.85 mL). The mixture was treated with H2O (2.283 mL), 2-methylbut-2-ene (1.1 mL, 1.370 mmol), sodium hydrogenphosphate (389 mg, 2.74 mmol). Finally, sodium chlorite (372 mg, 4.11 mmol) was added in one portion. The mixture was heated to 70° C. in the microwave for 2 h. An aliquot of the reaction mixture was analyzed by LC-MS. LC-MS analysis showed one major product with the correct mass for the desired product. The reaction mixture was diluted with EtOAc (15 mL) and washed with 1 M HCl (1×5 mL), H2O (1×5 mL) and saturated NaCl (1×5 mL). HPLC analysis of the combined aqueous washes showed only trace amounts of the desired product. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo to give 414 mg of a cream colored solid. The crude material was stirred with Et2O (˜5 mL). After stiffing for ˜3 h the solid was removed by vacuum filtration washing with Et2O. The solid was air-dried for several hours and then dried under vacuum. The title compound (348 mg, >99%) was isolated as a white solid: mp 149-151° C.; 1H NMR (400 MHz, CDCl3) δ 11.60 (s, 1H), 4.97 (s, 2H), 1.41 (d, J=1.5 Hz, 9H); 19F NMR (376 MHz, CDCl3) δ −132.92; 13C NMR (101 MHz, CDCl3) δ 161.62, 151.12, 149.21, 146.63, 141.58, 117.18, 36.69, 28.37.