Triethylamine → HCID 57724946, compound

HRID 1987806Notes

Reaction equation

HRID 1987806 reaction equation
[CH3:1][C:2]([CH3:11])([CH3:10])[CH2:3][O:4]/[CH:5]=[CH:6]/[C:7](=[O:9])[CH3:8].C(N(CC)CC)C.FC(F)(F)S(O[Si:25]([CH3:28])([CH3:27])[CH3:26])(=O)=O.C(=O)(O)[O-].[Na+]>C(OCC)C.C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]([CH3:11])([CH3:10])[CH2:3][O:4]/[CH:5]=[CH:6]/[C:7](=[CH2:8])[O:9][Si:25]([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 57724954HCID 57724954, compound

Product 1

HCID 57724946HCID 57724946, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

(E)-4-(2,2-dimethylpropoxy)but-3-en-2-one (14 g, 90 mmol) and triethylamine (10 g, 101 mmol) were combined in ethyl ether (200 mL). Trimethylsilyl trifluoromethanesulfonate (20 g, 90 mmol) (Aldrich) in carbon tetrachloride (30 mL) was added at −5° C. over 0.5 hr. This was stirred for 0.5 hr at 0° C. This was poured into cold 5% sodium bicarbonate (50 mL) and the organics were extracted into hexane. This was washed with saturated aqueous sodium chloride, dried (MgSO4), and evaporated to give 21 g of [(E)-3-(2,2-dimethylpropoxy)-1-methylene-allyloxy]trimethylsilane.

Workup

  1. extractionthe organics were extracted into hexane
  2. washThis was washed with saturated aqueous sodium chloride
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-6d5d28ec0fd545a4ac63a1a4f37966e8
Source dataset
uspto-grants-2009_06
Patent number
US07553833B2

Reaction notes

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