The synthetic method of 3-aminomethyltetrahydrofuran
A technology for aminomethyltetrahydrofuran and nitromethyltetrahydrofuran, which is applied in the field of synthesizing 3-aminomethyltetrahydrofuran, can solve the problems of unsuitability for industrial production, long synthesis route, improper operation, etc., and achieves low cost of raw materials and short synthesis route. , The effect of low production cost
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Embodiment 1
[0037] Synthesis of 2-nitromethyl-1, 4-diethyl succinate:
[0038] Add potassium carbonate (10.4 g, 0.075 mol) to nitromethane (100 mL), then add diethyl maleate (43.0 g, 0.25 mol), after the addition, stir at room temperature to react for 12 h, filter out potassium carbonate , Concentrated and recovered nitromethane, the residue was distilled under reduced pressure to obtain 54.0 g of diethyl 2-nitromethyl-1,4-succinate, with a yield of 92.6%. 1 H NMR (400MHz, CDCl 3 ) δ 4.82-4.77 (dd, J = 8.0, 4.0 Hz, 1H), 4.71-4.66 (dd, J = 8.0,4.0 Hz, 1H), 4.21-4.17 (q, J = 4.0 Hz, 2H), 4.16-4.12 (q, J = 4.0 Hz, 2H),3.55-3.49 (m, 1H), 2.84-2.79 (dd, J = 4.0, 4.0 Hz, 1H), 2.71-2.65 (dd, J =8.0, 8.0 Hz, 1H), 1.26-1.22 (t, J = 8.0 Hz, 3H); 13 C NMR (101 MHz, CDCl 3 ) δ170.49, 170.23, 74.41, 61.84, 61.16, 39.05, 32.87, 14.02, 13.88.
[0039] Synthesis of 2-nitromethyl-1, 4-butanediol:
[0040] Add 2-nitromethyl-1,4-diethyl succinate (46.6 g, 0.20 mol) in EtOH (42 mL) solution slowly and dropwi...
Embodiment 2
[0046] Synthesis of 2-nitromethyl-1, 4-diethyl succinate:
[0047] Add potassium carbonate (6.9 g, 0.05 mol) to nitromethane (75 mL), then add diethyl maleate (43.0 g, 0.25 mol), after the addition, stir at room temperature to react for 14 h, filter out potassium carbonate , Concentrated and recovered nitromethane, the residue was distilled under reduced pressure to obtain 52.9 g of diethyl 2-nitromethyl-1,4-succinate, with a yield of 90.7%.
[0048] Synthesis of 2-nitromethyl-1, 4-butanediol:
[0049] Add 2-nitromethyl-1,4-diethyl succinate (46.6 g, 0.20 mol) in MeOH (42 mL) solution slowly and dropwise to sodium borohydride (13.6 g, 0.36 mol) in tetrahydrofuran (180 mL) in the suspension, keep the reaction temperature at 20~30 during the dropping process o Between C. The dripping is complete, keep at this temperature and stir the reaction for 4 h, then heat up to 60 o C reflux and stir the reaction for 6 h. Then it was cooled with an ice-water bath, and concentrated hydrochloric...
Embodiment 3
[0055] Synthesis of 2-nitromethyl-1,4-dibutyl succinate:
[0056] Add potassium fluoride (3.5 g, 0.06 mol) to nitromethane (100 mL), then add dibutyl maleate (45.7 g, 0.2 mol), after the addition, stir the reaction at room temperature for 13 h, concentrate to recover the nitrate The residue was dissolved in dichloromethane (100 mL), and then washed with water. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, and distilled under reduced pressure to obtain 2-nitromethyl-1,4-butane. Dibutyl diacid 49.5 g, the yield was 85.5%.
[0057] Synthesis of 2-nitromethyl-1, 4-butanediol:
[0058] Add 2-nitromethyl-1,4-dibutyl succinate (57.9 g, 0.2 mol) in MeOH (42 mL) solution slowly and dropwise to potassium borohydride (21.6 g, 0.4 mol) in tetrahydrofuran (180 mL) in the suspension, keep the reaction temperature at 15~30 during the dropping process o Between C. The dripping is complete, keep at this temperature and stir the reaction for 4 h, then heat up to...
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