Ethanol → 2-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)ethyl methanesulfonate

HRID 333674노트

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HRID 333674 반응식
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][S:6]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20]OS(C)(=O)=O)(=[O:8])=[O:7].C(O)C>O>[CH3:5][S:6]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][N:1]=[N+:2]=[N-:3])(=[O:8])=[O:7]

참가 물질

5

반응물 3

HCID 702EthanolHCID 33557Sodium AzideHCID 36378751,11-Bis(methanesulfonyloxy)-3,6,9-trioxandecane

생성물 1

HCID 148276732-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)ethyl methanesulfonate수율 47.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Sodium azide (1.0 g) is added to a solution of tetraethyleneglycol dimethanesulphonate (5.25 g, 15 mmol), obtained according to A. W. Chwabacher et al. (J. Org. Chem. 1998, 65(5), 1717), in 18 mL of 95° ethanol. The reaction mixture is taken to reflux for 24 hours. Then the solvent is evaporated off, the reaction crude is added to 100 mL of salt water and extracted with ether (3×100 mL). The organic phase is dried over MgSO4, filtered and concentrated under reduced pressure. The residue obtained is purified by chromatography on a silica column using a gradient of AcOEt in hexane (1/1 to 3/1) as eluents. 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl mono-methanesulphonate 47 (2.10 g, 47%) is obtained, which is used directly in the following stage.

후처리

  1. customobtained
  2. temperatureto reflux for 24 hours
  3. customThen the solvent is evaporated off
  4. customthe reaction crude
  5. extractionextracted with ether (3×100 mL)
  6. dry with materialThe organic phase is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue obtained
  10. customis purified by chromatography on a silica column

출처 및 근거

ORD 기록
ord-417ed977ad874366a400f6d33711f85c
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883763B2

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