反应详情

A sol. of 2-chloro-3,6-difluoro-benzaldehyde oxime (21.3 g, 111 mmol) in DMF (66.7 mL) was added dropwise to a sol. of NCS (14.9 g, 111 mmol) and pyridine (1.78 mL) in DMF (222 mL). The mixture was stirred for 1 h at rt, and a sol. of propargyl alcohol (4.99 g, 89.1 mmol) in DMF (71 mL) was dropwise added. The reaction mixture was heated to 85° C., and a sol. of Et3N (15.5 mL, 111 mmol) in DMF (89.3 mL) was slowly added. The reaction mixture was stirred at 85° C. for 60 min, and was allowed to cool to rt. The mixture was diluted with water (533 mL), and was extracted with EtOAc (2×). The combined org. extracts were washed with water and brine, were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 40:60) yielded the title compound (17.0 g, 78%). LC-MS: tR=0.84 min; ES+: 287.12.

1. temperatureThe reaction mixture was heated to 85° C.
2. stirringThe reaction mixture was stirred at 85° C. for 60 min
3. temperatureto cool to rt
4. extractionwas extracted with EtOAc (2×)
5. washextracts were washed with water and brine
6. dry with materialwere dried over Na2SO4
7. filtrationfiltered
8. customthe solvents were removed under reduced pressure
9. customPurification of the residue by FC (EtOAc/heptane 40:60)