反应详情

This procedure is derived from the general method of T. Taguchi, et al. (Tetrahedron Lett., 1986,27,6103-6106). Ethyl difluoroiodoacetate (0.355 mL, 651 mg, 2.60 mmol) was added to a rapidly stirred suspension of copper powder (333 mg, 5.24 mmol) in DMSO (6.5 mL) at RT. After 50 min., 3-bromo-6-methylpyridazine (300 mg, 1.73 mmol) was added in DMSO (1.0 mL). After 20 h, the mixture was transferred to a separatory funnel containing water (25 mL) and saturated aq. NH4Cl (25 mL), and extracted with EtOAc (2×50 mL). The organic extracts were washed with saturated aq. NaCl, dried (Na2SO4), decanted, and evaporated. Purification by flash column chromatography on silica gel, eluting with 70:30 v/v hexanes/EtOAc, gave 363 mg of the title compound as an amber liquid. For the title compound: 1H NMR (500 MHz, CDCl3) δ 7.79 (d, J=9, 1H), 7.53 (d, J=9, 1H), 4.43 (q, J=7, 2H), 2.82 (s, 3H), 1.38 (t, J=7, 3H).

1. waitAfter 20 h
2. customthe mixture was transferred to a separatory funnel
3. extractionextracted with EtOAc (2×50 mL)
4. washThe organic extracts were washed with saturated aq. NaCl
5. dry with materialdried (Na2SO4)
6. customdecanted
7. customevaporated
8. customPurification by flash column chromatography on silica gel
9. washeluting with 70:30 v/v hexanes/EtOAc