Method for preparing heterocyclic carbonate
A kind of technology of aromatic ring group and compound, applied in the field of preparation of heterocyclic carbonate, can solve problems such as difficult preparation
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Embodiment 1
[0022] HOCH 2 CH 2 SeSeCH 2 CH 2 Synthesis of OH:
[0023] Sodium borohydride (3.5g, 0.092mol) and deionized water (150mL) were placed in a 500mL reaction flask, stirred to form a colorless transparent solution, then selenium powder (7.3g, 0.092mol) was added, and reacted at room temperature for 30min to obtain Reddish-brown Na 2 Se 2 Solution is directly used in next step reaction (when the mol ratio of sodium borohydride and selenium is 2: 1 or when greater than 2: 1, can obtain Na 2 Se solution, can be used to synthesize HOCH 2 CH 2 SCH 2 CH 2 OH (abbreviated as "monoselenoethanol").
[0024] Under the protection of argon, a THF solution (140 mL) of bromoethanol (11.6 g, 0.092 mol) was added and reacted at 50° C. for 6 h. The reaction was stopped, extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, and separated through a silica gel column (eluent was ethyl acetate:dichloromethane=1:1 (v / v)) to obtain compound (HOCH 2 CH...
Embodiment 2
[0026] Synthesis of compounds shown in formula Ⅰ-1:
[0027]
[0028] Add biselenoethanol (0.5g, 2.0mmol) into the pre-baked reaction bulb for 3 times, vacuumize for 5h to completely remove residual moisture, then add 250mL of anhydrous toluene, stir until a yellow transparent solution is formed. Diphenyl carbonate (0.65g, 3.0mmol) and 0.65g lipase Novozym435 were added and reacted at 70°C for 12h. The reaction was stopped, the enzyme was removed by filtration, the toluene was removed by distillation under reduced pressure, and the crude product was obtained through silica gel column separation (the eluent was dichloromethane), which was further purified by ethyl acetate recrystallization to obtain the target compound (compound shown in formula I-1). Yield 53.2%.
[0029] 1 H NMR (400MHz, CDCl 3 ,δ,ppm):4.41(t,J=6.8Hz,8H,a),3.25(t,J=6.8Hz,8H,b);
[0030] 13 C NMR (400MHz, CDCl 3 ,δ,ppm): 154.59,67.39,27.48;
[0031] HRMS(ESI,m / z):M+C 10 h 16 o 6 Se 4 Na calculate...
Embodiment 3
[0033] In the synthesis of compound shown in formula Ⅰ-1, the impact of toluene consumption on product yield:
[0034] Except that the amount of toluene was different, other conditions and reagents were the same as in Example 2, and the effect of the amount of toluene on the synthesis and yield of the compound was studied. The specific results are shown in Table 1..
[0035] Table 1.
[0036]
[0037] a The amount of anhydrous toluene needed per gram of compound shown in formula II
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