反应详情

Dissolved 2,5-dichloroquinoline-3-carbaldehyde (2.46 g, 11 mmol) in THF (70 mL) and submerged in an ice-bath. Added methylmagnesium bromide (5.4 mL, 16 mmol) and removed the ice-bath. After 10 min. the reaction mixture was poured into 1.0 N HCl and extracted with EtOAc. The organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was chromatographed on 80 g silica gel column with 0-40% EtOAc:Hex. The desired fractions were combined and concentrated to yield an off white, crystalline solid. 1H NMR (400 MHz, DCM-d2) δ ppm 1.60 (d, J=6.26 Hz, 3H) 2.35 (br. s., 1H) 5.36 (q, J=6.39 Hz, 1H) 7.61-7.67 (m, 2H) 7.87-7.94 (m, 1H) 8.75 (s, 1H). LC-MS (+esi, M+H+=242.1).

1. customsubmerged in an ice-bath
2. extractionextracted with EtOAc
3. dry with materialThe organic layer was dried with sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was chromatographed on 80 g silica gel column with 0-40% EtOAc
7. concentrationconcentrated
8. customto yield an off white, crystalline solid