Method for synthesizing benzofuran derivative by taking alpha-phenoxy-ketone as raw material
A technology of benzofuran and phenoxy ketone, which is applied in the field of preparation of benzofuran derivatives, can solve the problems of harsh reaction conditions, energy consumption, low reaction yield and the like, achieves less side reactions, easy separation and purification, and reaction Simple system effect
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Embodiment 1
[0025] Embodiment 1: the synthesis of benzofuran derivative II a
[0026]
[0027] In a 25mL two-necked flask under nitrogen protection, add α-phenoxyketone I a (1mmol) and dry dichloromethane (5mL), then slowly add TiCl 4 (1mmol) and dichloromethane (5mL) mixed solution. After the reaction was completed (monitored by TLC), it was quenched by adding saturated aqueous ammonium chloride solution (10 mL), and extracted with dichloromethane (3×10 mL). The dichloromethane solution obtained by the mixed extraction was concentrated under reduced pressure, and then separated by silica gel column chromatography to obtain the target product II a as a yellow liquid with a yield of 80%.
[0028] 1 H NMR (600MHz, CDCl 3 )δ7.48-7.39(m, 1H), 7.39-7.32(m, 1H), 7.23-7.15(m, 2H), 2.38(d, J=0.6Hz, 3H), 2.16(d, J=0.7Hz ,3H); 13 C NMR (150MHz, CDCl 3 )δ152.76, 149.44, 129.44, 121.95, 120.92, 117.47, 109.36, 108.67, 10.77, 6.89.
Embodiment 2
[0029] Embodiment 2: the synthesis of benzofuran derivative II b
[0030]
[0031] In a 25 mL two-necked flask under nitrogen protection, α-phenoxyketone I b (1 mmol) and dry dichloromethane (5 mL) were added, and then TiCl was slowly added dropwise 4 (1mmol) and dichloromethane (5mL) mixed solution. After the reaction was completed (monitored by TLC), it was quenched by adding saturated aqueous ammonium chloride solution (10 mL), and extracted with dichloromethane (3×10 mL). The dichloromethane solution obtained by the mixed extraction was concentrated under reduced pressure, and then separated by silica gel column chromatography to obtain the target product II b as a colorless liquid with a yield of 82%.
[0032] 1 H NMR (600MHz, CDCl 3 )δ7.23(d, J=8.3Hz, 1H), 7.18(s, 1H), 7.00(dd, J=8.2, 1.3Hz, 1H), 2.43(s, 3H), 2.36(s, 3H), 2.12(s, 3H); 13 C NMR (150MHz, CDCl3 )δ152.18, 150.58, 131.32, 130.54, 124.10, 118.50, 109.88, 109.44, 21.38, 11.84, 7.94.
Embodiment 3
[0033] Embodiment 3: the synthesis of benzofuran derivative II c
[0034]
[0035] In a 25mL two-necked flask under nitrogen protection, add α-phenoxyketone Ic (1mmol) and dry dichloromethane (5mL), then slowly add TiCl 4 (1mmol) and dichloromethane (5mL) mixed solution. After the reaction was completed (monitored by TLC), it was quenched by adding saturated aqueous ammonium chloride solution (10 mL), and extracted with dichloromethane (3×10 mL). The dichloromethane solution obtained by the mixed extraction was concentrated under reduced pressure, and then separated by silica gel column chromatography to obtain the target product II c as a light yellow liquid with a yield of 83%.
[0036] 1 H NMR (600MHz, CDCl 3 )δ7.25(d, J=8.8Hz, 1H), 6.86(d, J=2.6Hz, 1H), 6.79(dd, J=8.8, 2.6Hz, 1H), 3.85(s, 3H), 2.36( s, 3H), 2.12(s, 3H); 13 C NMR (150MHz, CDCl 3 )δ154.54, 150.41, 147.66, 129.98, 110.04, 109.71, 108.83, 100.63, 54.94, 10.89, 6.96; HRMS (ESI) calcd for C 11 h 13 o ...
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