Trimethylsilyl triflate → (3-Ethoxy-1-methylene-allyloxy)-trimethyl-silane

HRID 1987802Notes

Reaction equation

HRID 1987802 reaction equation
[CH2:1]([O:3][CH:4]=[CH:5][C:6](=[O:8])[CH3:7])[CH3:2].[Si:9](OS(C(F)(F)F)(=O)=O)([CH3:12])([CH3:11])[CH3:10]>C1COCC1>[CH2:1]([O:3][CH:4]=[CH:5][C:6](=[CH2:7])[O:8][Si:9]([CH3:12])([CH3:11])[CH3:10])[CH3:2]

Participants

4

Reactant 2

HCID 65367Trimethylsilyl triflateHCID 158716554-Ethoxy-but-3-en-2-one

Product 1

HCID 85441339(3-Ethoxy-1-methylene-allyloxy)-trimethyl-silaneYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 250 mL three-necked flask under N2 atomosphere, to a solution of 7.2 g of 4-ethoxy-but-3-en-2-one (63 mmol, 1 eq) and 12.7 g of TEA (126 mmol, 2 eq) in THF at −78° C., was added 21 g of TMSOTf (95 mmol, 1.5 eq) dropwise in 40 mins. Stirring was continued for 60 mins at 0˜−30° C. After the conversion was complete (check by NMR), the reaction was quenched with 5% NaHCO3, extract with Hexane and dried over Na2SO4. After remove the solvent the crude product was purified with redistillation (oil pump, <<1 mmbar: Bp, 40° C., Toluene; Bp, 115° C., product) to give 9.1 g pure product. Yield: 72.2%.

Workup

  1. customthe reaction was quenched with 5% NaHCO3
  2. extractionextract with Hexane
  3. dry with materialdried over Na2SO4
  4. customAfter remove the solvent the crude product
  5. distillationwas purified with redistillation (oil pump, <<1 mmbar: Bp, 40° C., Toluene; Bp, 115° C., product)

Sources & evidence

ORD record
ord-482f8fbfd6d340628d79f328486af323
Source dataset
uspto-grants-2009_06
Patent number
US07553833B2

Reaction notes

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