Methyl iodide → ethyl 2-(trimethylsilyl)propanoate

HRID 1493434Notes

Reaction equation

HRID 1493434 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.CCCCCC.[CH3:19][Si:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH3:22])[CH3:21].CI>C1COCC1>[CH3:19][Si:20]([CH3:22])([CH3:21])[CH:23]([CH3:1])[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 77687Ethyl trimethylsilylacetateHCID 178418244HCID 178418244, compound

Product 1

HCID 268025ethyl 2-(trimethylsilyl)propanoateYield 44.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 21.8 mL (0.156 mole) of diisopropylamine in 100 mL of THF at 0° was added 0.156 mole of butyl lithium/hexane. After 30 minutes at 0°, the solution was cooled to -78°, and 25 g (0.156 mole) of ethyl trimethylsilylacetate was added. After 30 minutes at -78°, 22.7 g (10 mL, 0.16 mole) of methyl iodide was added. After warming to room temperature, the mixture was filtered, and the filtrate was evaporated. The residue was treated with hexane and filtered under argon The hexane layer of the filtrate was concentrated and distilled in a small Vigreux column to give 12 g of ethyl 2-trimethylsilylpropionate, b.p. 61.4°/15 mm.

Workup

  1. temperaturethe solution was cooled to -78°
  2. waitAfter 30 minutes at -78°
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated
  5. additionThe residue was treated with hexane
  6. filtrationfiltered under argon The hexane layer of the filtrate
  7. concentrationwas concentrated
  8. distillationdistilled in a small Vigreux column

Sources & evidence

ORD record
ord-9a1e3649ed1747209ab50c4212a0dcfb
Source dataset
uspto-grants-1991_06
Patent number
US05021524

Reaction notes

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