Ethyl formate → 1,3-Bis(trimethylsilyl)propan-2-ol

HRID 610400Notes

Reaction equation

HRID 610400 reaction equation
C([O:3][CH2:4][CH3:5])=O.[CH3:6][Si:7]([CH2:10][Mg]Cl)([CH3:9])[CH3:8].Cl.[NH4+]>C(OCC)C>[CH3:6][Si:7]([CH3:10])([CH3:9])[CH2:8][CH:4]([OH:3])[CH2:5][Si:7]([CH3:9])([CH3:8])[CH3:6]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 21905121Ammonium hydrochlorideHCID 178418680HCID 178418680, compound

Product 1

HCID 126567131,3-Bis(trimethylsilyl)propan-2-olYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl formate (0.1 mol) was slowly added to 0.3 mol of trimethylsilylmethyl magnesium chloride solution dissolved in diethyl ether which was contained in a 500 ml flask. The mixture was allowed to react under reflux for about 24 hours. After hydrolyzing the reactant using ammonium hydrochloride solution, the obtained reaction product was separated and purified by a vacuum distillation and a 70 percent yield was obtained. The structure of the obtained distillates was analyzed using NMR and a spectroscopic method of FT-IR spectroscopy.

Workup

  1. customwas contained in a 500 ml flask
  2. customto react
  3. temperatureunder reflux for about 24 hours
  4. customthe obtained reaction product
  5. customwas separated
  6. distillationpurified by a vacuum distillation
  7. customa 70 percent yield was obtained

Sources & evidence

ORD record
ord-169259283d3540b3b4ec943f1d644776
Source dataset
uspto-grants-1999_12
Patent number
US05998557

Reaction notes

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