反应详情

温度

63 °C

1-chloro-3-(4-fluorophenyl)hex-5-en-3-ol (58 mg, 0.25 mmol), 1-methyl-1-phenylhydrazine (500 mg, 4.09 mmol), and tetrabutylammonium iodide (92 mg, 0.25 mmol) were combined and heated in a microwave for 50 min at 63° C. The crude mixture was filtered and purified twice by chromatography on a silica gel cartridge eluted with an EtOAc/hexanes gradient to remove 1-methyl-1-phenylhydrazine. The residue was dissolved in Et2O and washed with 1 M aq HCl. The aqueous layer was treated with 1 M aq NaOH until a pH of 4 was reached, then extracted with Et2O. The organic layer was evaporated and the residue was further purified by preparative HPLC to provide 3-(4-fluorophenyl)-1-(2-methyl-2-phenylhydrazinyl)hex-5-en-3-ol (6 mg). LC-MS Method 1 m/z=315 (M+1).

1. filtrationThe crude mixture was filtered
2. custompurified twice by chromatography on a silica gel cartridge
3. washeluted with an EtOAc/hexanes gradient
4. customto remove 1-methyl-1-phenylhydrazine
5. dissolutionThe residue was dissolved in Et2O
6. washwashed with 1 M aq HCl
7. additionThe aqueous layer was treated with 1 M aq NaOH until a pH of 4
8. extractionextracted with Et2O
9. customThe organic layer was evaporated
10. customthe residue was further purified by preparative HPLC