Tin tetrachloride → 3-[2-Azido-2-(2-hydroxyethoxy)ethoxy]benzoic acid ethyl ester

HRID 1923445Notes

Reaction equation

HRID 1923445 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH:13]2[O:17][CH2:16][CH2:15][O:14]2)[CH:6]=1)[CH3:2].[N:19]([Si](C)(C)C)=[N+:20]=[N-:21].Cl[Sn](Cl)(Cl)Cl>CO>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH:13]([N:19]=[N+:20]=[N-:21])[O:14][CH2:15][CH2:16][OH:17])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 78378AzidotrimethylsilaneHCID 17999177Ethyl 3-((1,3-dioxolan-2-yl)methoxy)benzoate

Product 1

HCID 597717683-[2-Azido-2-(2-hydroxyethoxy)ethoxy]benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 3-([1,3]-dioxolan-2-ylmethoxy)-benzoic acid ethyl ester (2.02 g, 8 mmol) and azidotrimethylsilane (1.17 ml, 8.8 mmol) was added SnCl4 (60 μl) at room temperature under nitrogen. After 2 hr, 2% aqueous methanol (10 ml) was added to the reaction mixture and the reaction was stirred at room temperature for 30 minutes. All the solvents were evaporated under reduced pressure. The residue was co-evaporated with ethanol (2×10 ml). The residue was purified by column chromatography (3×20 cm). The product was eluted with 0 to 1% methanol in DCM. The title compound was obtained as a colourless oil (2.01 g, 85.1%). APCI-MS, m/z 267.90 (M−N2+1).

Workup

  1. customAll the solvents were evaporated under reduced pressure
  2. customThe residue was purified by column chromatography (3×20 cm)
  3. washThe product was eluted with 0 to 1% methanol in DCM

Sources & evidence

ORD record
ord-9ae0b17edb614f39b01cce98bf776822
Source dataset
uspto-grants-2012_05
Patent number
US08178360B2

Reaction notes

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