Potassium Carbonate → 7-benzyloxyl-2-oxo-2H-1-benzopyran-3-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:16])[O:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([OH:15])[CH:9]=2)=[O:4].C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:16])[O:7][C:8]2[CH:9]=[C:10]([O:15][CH2:14][C:13]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:11]=[CH:12][C:13]=2[CH:14]=1)=[O:4]Participants
3
Conditions
- Temperature
- 70 °C
Procedure
7-hydroxyl-3-coumarin carboxylic acid methyl ester (0.2g, 1 mmol) is dissolved in N,N′-dimethyl formamide (2 mL), and bromobenzyl (0.36 ml, 3 mmol) and levigated potassium carbonate (0.5 g) are added into. The resulting mixture is stirred for 12 hours at 70° C. After adding 10 mL of water, extraction is conducted with ethyl acetate, and all of ethyl acetate are combined, followed by washing with water, drying on anhydrous sodium sulfate. Then the solution is concentrated under reduced pressure to approximately 5 mL and is placed to separate out a solid, followed by filtering under reduced pressure to obtain 0.21 g of the captioned compound, yield: 67.7%. m.p.129-130° C. 1H NMR(CDCl3): δ=3.92(s, 3H), 5.19(s, 2H), 6.85(d, J=2.4 Hz, 1H), 6.95(dd, J=8.8 Hz, 2.4 Hz, 1H), 7.40(m, 5H), 7.52(d, J=8.8 Hz, 1H), 8.55(s, 1H); Elements Analysis, C18H14O5 (310): Calculated C, 69.68; H, 4.52. Found C, 69.63; H, 4.51; IR(KBr) : 3054.7, 2948.7, 1749.1, 1697.1, 1610.3, 1558.2, 1500.4, 1438.7, 1378.9, 1226.5, 1116.6, 1026, 794.5, 725.1, 692.3, 636.4 cm−1; EI-MS(m/z): 310(12, M+), 91(100).