Sodium Azide → 3,5-didecoxybenzyl Azide

HRID 2055754노트

반응식

HRID 2055754 반응식
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:19]=1)[CH2:15]Cl)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[N-:31]=[N+:32]=[N-:33].[Na+]>CN(C=O)C>[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:19]=1)[CH2:15][N:31]=[N+:32]=[N-:33])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 693060093,5-didecoxybenzyl Chloride

생성물 1

HCID 862391583,5-didecoxybenzyl Azide수율 93.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

3,5-Didecoxybenzyl chloride (14.4 g, 32.8 mmol) was dissolved in DMF (50 mL) in a 250 mL RBF. Sodium azide (4.26 g, 65.6 mmol) and a magnetic stir bar were added to the RBF. The RBF was heated to just below boiling of the DMF using a heat gun. The reaction mixture was then stirred at room temperature until cool to the touch. Heating and cooling were repeated 3 times. Thin layer chromatography in hexanes showed the presence of a starting material. A heating mantel was used to gently heat the RBF. After 1 hour, thin layer chromatography showed no starting material present. The contents of the RBF were transferred to a separatory funnel. Ether (250 mL) and distilled H2O (250 mL) were added to the funnel. The aqueous layer was washed 2 times with ether (250 mL). The ether layers were combined and washed 2 times with saturated ammonium chloride solution (125 mL) and once with saturated sodium chloride solution (125 mL). The ether layer was then dried with magnesium sulfate, gravity filtered and concentrated using rotary evaporation. High vacuum was then used to remove trace amounts of the ether giving. There was a 13.6 g yield or a 93.1% yield of the derivative. The NMR characterization data for this derivative is as follows. 1NMR (300 MHz, CDCl3): 0.88 (t, J=6.6, 6H, CH2CH3), 1.27-1.43 (m, 28H, CH2(CH2)7), 1.76 (p, J=6.6, 4H, OCH2CH2), 3.92 (t, J=6.6, 4H, OCH2), 4.21 (s, 2H, ArCH2N3), 6.42-6.44 (m, 3H, ArH). 13C NMR (75 MHZ, CDCl3): 14.23, 22.79, 26.13, 29.31, 29.45, 29.49, 29.68, 29.71, 32.01, 55.01, 65.97, 68.19, 101.08, 106.52, 137.45, 160.68.

후처리

  1. temperatureuntil cool to the touch
  2. temperatureHeating
  3. temperaturecooling
  4. temperatureto gently heat the RBF
  5. customThe contents of the RBF were transferred to a separatory funnel
  6. distillationEther (250 mL) and distilled H2O (250 mL)
  7. additionwere added to the funnel
  8. washThe aqueous layer was washed 2 times with ether (250 mL)
  9. washwashed 2 times with saturated ammonium chloride solution (125 mL)
  10. dry with materialThe ether layer was then dried with magnesium sulfate, gravity
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customevaporation
  14. customto remove trace amounts of the ether giving
  15. customyield

출처 및 근거

ORD 기록
ord-4d0294a1d16748c281cc9d7183205428
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07332529B2

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