| 65% |
Stage #1: 1,3-bis(selenocyanato)propane With sodium hydroxide In ethanol; water at 20℃; for 2h;
Stage #2: With sodium tetrahydroborate In ethanol; water at 20 - 50℃; for 2h;
Stage #3: sodium 2-bromoacetate In ethanol; water at 20℃; |
|
| 65% |
Stage #1: 1,3-bis(selenocyanato)propane With water; sodium hydroxide In ethanol at 20 - 25℃; for 2h;
Stage #2: With sodium tetrahydroborate; water In ethanol at 20 - 50℃; for 2h;
Stage #3: sodium 2-bromoacetate |
To a solution of NaOH (0.500 g, 12.50 mmol) in 15 ml of a mixture ethanol/water (2/1) was added the above prepared propylene diselenocyanate (0.466 g, 1.85 mmol) and the mixture was stirred for 2 h at room temperature to give an orange solution. NaBH4 (0.500 g, 13.22 mmol) was added and the mixture was stirred for 1 h at room temperature and a further 1 h at 50 °C to give an orange solution and a yellow precipitate. Sodium 2-bromoacetate (0.596 g, 3.71 mmol) was added and the mixture was stirred overnight at room temperature. The white precipitate was removed by filtration and the colorless solution was concentrated under reduced pressure to 5 ml. The pH was adjusted to pH 1 by addition of a 6 M HCI solution. The resulting white precipitate and the remaining aqueous solution were extracted with CH2CI2 and the combined organic layers were washed with water and dried over MgS04. After removal of the solvents under reduced pressure, the residual white solid was washed with cyclohexane and dried under vacuum to give the desired product 4. Yield: 0.380 g (65%); m.p. 75 °C; IR 2860 (m), 2640 (m), 2510 (m), 1678 (s), 1425 (m), 1389 (m), 1271 (s), 1227 (m), 1178 (m), 1159 (m), 1116 (m), 935 (s), 765 (m), 747 (m), 648 (s) cm" 1; JH NMR (DMSO-cfc): δ 2.00 (quint., 2 H, CH2CH2CH2), 2.80 (t, 3 H = 6.8 Hz, 4 H, CH2CH2CH2), 3.20 [s (93%) and d (7%), 2 ¾H = 15.1 Hz, 4 H, SeCH2C02H], 12.50 (br s, 2 H, C02H); 13C NMR (DMSO-4): δ 22.5 [s (93%) and d (7%), /¾ = 67.0 Hz, SeCH2], 24.3 [s (93%) and d (7%), = 61.8 Hz, SeCH2], 29.6 (s, CH2CH2CH2), 172.7 (s, C02H). |
| 65% |
Stage #1: 1,3-bis(selenocyanato)propane With water; sodium hydroxide In ethanol at 20 - 25℃; for 2h;
Stage #2: With sodium tetrahydroborate; water In ethanol at 20 - 50℃; for 2h;
Stage #3: sodium 2-bromoacetate |
To a solution of NaOH (0.500 g, 12.50 mmol) in 15 ml of a mixture ethanol/water (2/1) was added the above prepared propylene diselenocyanate (0.466 g, 1.85 mmol) and the mixture was stirred for 2 h at room temperature to give an orange solution. NaBH4 (0.500 g, 13.22 mmol) was added and the mixture was stirred for 1 h at room temperature and a further 1 h at 50 °C to give an orange solution and a yellow precipitate. Sodium 2-bromoacetate (0.596 g, 3.71 mmol) was added and the mixture was stirred overnight at room temperature. The white precipitate was removed by filtration and the colorless solution was concentrated under reduced pressure to 5 ml. The pH was adjusted to pH 1 by addition of a 6 M HCl solution. The resulting white precipitate and the remaining aqueous solution were extracted with CH2Cl2 and the combined organic layers were washed with water and dried over MgSO4. After removal of the solvents under reduced pressure, the residual white solid was washed with cyclohexane and dried under vacuum to give the desired product 4. Yield: 0.380 g (65%); m.p. 75 °C; IR 2860 (m), 2640 (m), 2510 (m), 1678 (s), 1425 (m), 1389 (m), 1271 (s), 1227 (m), 1178 (m), 1159 (m), 1116 (m), 935 (s), 765 (m), 747 (m), 648 (s) cm-1; 1H NMR (DMSO-d6): δ 2.00 (quint., 2 H, CH2CH2CH2), 2.80 (t, 3JHH = 6.8 Hz, 4 H, CH2CH2CH2), 3.20 [s (93%) and d (7%), 2 J77SeH = 15.1 Hz, 4 H, SeCH2CO2H], 12.50 (br s, 2 H, CO2H); 13C NMR (DMSO-d6): δ 22.5 [s (93%) and d (7%), 2 J77SeH = 67.0 Hz, SeCH2], 24.3 [s (93%) and d (7%), J77SeH = 61.8 Hz, SeCH2], 29.6 (s, CH2CH2CH2), 172.7 (s, CO2H). |
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