Water soluble 3-ketocoumarins
A C1-C6, C5-C6 technology, applied in the field of novel 3-coumarin ketone, can solve the problems of harmfulness, cured film not suitable for the original purpose, food contamination, etc.
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Embodiment 1
[0119]
[0120] A small amount of 67.0 g (502.5 mmol) of aluminum chloride was added in small batches to 30.0 g (168.3 mmol) of ethyl 3-phenylpropionate and 24.0 g (175.8 mmol) of 3-chloro- A solution of methyl 3-oxopropionate in 250 mL of dichloromethane. After stirring at room temperature for 4 hours, the reaction was poured into ice and water, and the resulting mixture was stirred for 30 minutes. The organic phase was then separated, washed with water, dried over sodium sulfate, filtered and the solvent was removed by vacuum distillation to give 37.7 g of a yellow oil (80% yield).
[0121] 1 H-NMR (CDCl 3 , δppm): 1.22(t, 3H), 2.65(t, 2H), 3.05(t, 2H), 3.75(s, 3H), 3.98(s, 2H), 4.10(q, 2H), 7.30(d, 2H), 7.85(d, 2H).
Embodiment 2
[0123]
[0124] 34.1 g (122.5 mmol) of the compound of Example 1 and 0.86 g (10.1 mmol) of piperidine were added to a solution of 22.3 g (122.4 mmol) of 4.6-dimethoxy-2-hydroxy-benzaldehyde in 100 mL of ethanol. The mixture was stirred at reflux for 2 hours, then cooled to room temperature. The reaction product was recovered by filtration to obtain 25.0 g of a white-yellow solid (50% yield).
[0125] 1 H-NMR (CDCl 3 , δppm): 1.23(t, 3H), 2.65(t, 2H), 3.10(t, 2H), 3.89(m, 6H), 4.12(q, 2H), 6.30(d, 1H), 6.45(d, 1H), 7.30 (d, 2H), 7.79 (d, 2H), 8.40 (s, 1H).
Embodiment 3
[0127]
[0128] Add 1.27g (6.08mmol) butyltin oxide hydroxide hydrate in small batches to a mixture of 2.50g (6.09mmol) Example 2 compound and 4.87g (12.18mmol) polyethylene glycol 400 while stirring at 150°C . The mixture was stirred at 150° C. for 8 hours, and ethanol was removed by distillation. After cooling to room temperature, the reaction mixture was dissolved in dichloromethane and filtered. The filtrate was washed twice with water, dried over sodium sulfate, and the solvent was removed by vacuum distillation. The crude product was purified by flash column chromatography on silica gel (dichloromethane:methanol 95:5) to obtain 3.95 g of a tan oil (yield 85%).
[0129] 1 H-NMR (CDCl 3 , δppm): 2.70(t, 2H), 3.00(t, 2H), 3.50-3.70(m, 32H), 3.90(m, 6H), 4.20(t, 2H), 6.30(d, 1H), 6.45( d, 1H), 7.30 (d, 2H), 7.75 (d, 2H), 8.40 (s, 1H).
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