Sodium Hydroxide → HCID 45119275, compound

HRID 2275696Notes

Reaction equation

HRID 2275696 reaction equation
C([O:3][C:4](=[O:15])[CH2:5][O:6][CH2:7][CH2:8][O:9][CH:10]([N:12]=[N+:13]=[N-:14])[CH3:11])C.[OH-].[Na+]>C(O)C>[N:12]([CH:10]([O:9][CH2:8][CH2:7][O:6][CH2:5][C:4]([OH:15])=[O:3])[CH3:11])=[N+:13]=[N-:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59771764HCID 59771764, compound

Product 1

HCID 45119275HCID 45119275, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[2-(1-Azido-ethoxy)-ethoxy]-acetic acid ethyl ester (0.10 g, 0.46 mmol) was stirred with 4 M aqueous sodium hydroxide (1.15 ml, 4.6 mmol) and ethanol (1.15 ml) at room temperature. After 4 hrs, all the solvents were removed under reduced pressure and the residue was dissolved in 5 ml water. The solution was adjusted to pH 5 with 1 N KH2PO4 and then extracted with DCM (2×15 ml). The aqueous layer was then acidified with 1 N HCl to pH 2 and then extracted with DCM (3×25 ml). All the DCM extracts were combined, dried over MgSO4 and evaporated under reduced pressure. The title compound was obtained as a colourless solid (42 mg, 48.3%).

Workup

  1. customall the solvents were removed under reduced pressure
  2. dissolutionthe residue was dissolved in 5 ml water
  3. extractionextracted with DCM (2×15 ml)
  4. extractionextracted with DCM (3×25 ml)
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-133d8287b93342ad90b8eb24805fb4b1
Source dataset
uspto-grants-2015_09
Patent number
US09127314B2

Reaction notes

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