Water → Acetic acid, nitro-, 2-(trimethylsilyl)ethyl ester

HRID 1885365Notes

Reaction equation

HRID 1885365 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][N+:6]([O-:8])=[O:7])[CH3:2].[CH3:10][Si:11](C)([CH3:15])[CH2:12]CO.O>C1C=CC=CC=1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[N+:6]([CH2:5][C:4]([O:3][CH2:1][CH2:2][Si:11]([CH3:15])([CH3:12])[CH3:10])=[O:9])([O-:8])=[O:7]

Participants

6

Reactant 3

HCID 962WaterHCID 180132-(Trimethylsilyl)ethanolHCID 69379Ethyl nitroacetate

Product 1

HCID 11195084Acetic acid, nitro-, 2-(trimethylsilyl)ethyl esterYield 79%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 241BenzeneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of nitroacetic acid ethyl ester (5.0 g, 37.6 mmol) and 2-(trimethylsily)ethanol (7.27 g, 61 mmol) in dry benzene (100 mL) is added titanium tetraisopropoxide (1.05 q, 3.69 mmol) and the mixture is heated at reflux for 1 hour. The solution is cooled to 40° C. and water (2 mL) is added and stirring is continued for 10 minutes at room temperature. The solvents are evaporated and the residue is taken up in dichloromethane and dried over anhydrous magnesium sulfate. The mixture is filtered through a small pad of Celite and the solvent is evaporated. The residue is purified by distillation to give nitroacetic acid, 2-(trimethylsily)ethyl ester (6.10 g, 79%) as a colorless liquid. B.pt. 90°-95° C./0.3 mmHg.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 1 hour
  3. customThe solvents are evaporated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe mixture is filtered through a small pad of Celite
  6. customthe solvent is evaporated
  7. distillationThe residue is purified by distillation

Sources & evidence

ORD record
ord-bfeb235da7054ed3985136f1430d1ad5
Source dataset
uspto-grants-1992_09
Patent number
US05144034

Reaction notes

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