Azidotrimethylsilane → 3-(2-Azido-2-ethoxy-ethoxy)-benzoic acid ethyl ester

HRID 661186Notes

Reaction equation

HRID 661186 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH:13](OCC)[O:14][CH2:15][CH3:16])[CH:6]=1)[CH3:2].[N:21]([Si](C)(C)C)=[N+:22]=[N-:23]>Cl[Sn](Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH:13]([N:21]=[N+:22]=[N-:23])[O:14][CH2:15][CH3:16])[CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 597717613-(2,2-Diethoxy-ethoxy)-benzoic acid ethyl ester

Product 1

HCID 597717513-(2-Azido-2-ethoxy-ethoxy)-benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 24287Tin tetrachlorideSolvent

Procedure

To a mixture of 3-(2,2-diethoxy-ethoxy)-benzoic acid ethyl ester (1.128 g, 4 mmol) and azidotrimethylsilane (0.584 ml, 4.4 mmol) was added SnCl4 (40 μl) at room temperature. After 1 hr, the precipitates were filtered off and the filtrate was evaporated under reduced pressure. The residue was dissolved in methanol, after 10 minutes, solvent was removed under reduced pressure. The residue was purified by a column chromatography (3×20 cm). The product was eluted with 10% petroleum ether (60-80° C.) in DCM. The title compound was obtained as a colourless oil (0.909 g, 81.5%).

Workup

  1. filtrationthe precipitates were filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in methanol, after 10 minutes
  4. customsolvent was removed under reduced pressure
  5. customThe residue was purified by a column chromatography (3×20 cm)
  6. washThe product was eluted with 10% petroleum ether (60-80° C.) in DCM

Sources & evidence

ORD record
ord-22b74e61706540238ba2fc36ffea7bb2
Source dataset
uspto-grants-2011_12
Patent number
US08084590B2

Reaction notes

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