Triethylamine → HCID 59545178, compound

HRID 886682Notes

Reaction equation

HRID 886682 reaction equation
[C:1]([O:4][CH2:5][CH3:6])(=[O:3])[CH3:2].C(N([CH2:12][CH3:13])CC)C.FC(F)(F)S(O[Si:20](OS(C(F)(F)F)(=O)=O)([CH3:22])[CH3:21])(=O)=O>>[CH3:21][Si:20]([CH3:22])([CH2:2][C:1]([O:4][CH2:12][CH3:13])=[O:3])[CH2:2][C:1]([O:4][CH2:5][CH3:6])=[O:3]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11121822Dimethylsilanediyl bis(trifluoromethanesulfonate)

Product 1

HCID 59545178HCID 59545178, compoundYield 23%

Conditions

Temperature
0 °C

Procedure

An oven-dried 100 mL-RB flask is charged with ethyl acetate (5.3 g, 0.06 mol), and triethylamine (6.1 g, 0.06 mol). The flask is then cooled in an ice-water bath, and dimethylsilanediyl bis(trifluoromethanesulfonate) (10.7 g, 0.03 mol) is added dropwise. After stirring at 0° C. for 1 h, the mixture is warmed up to room temperature and stirred overnight. The mixture is poured into ice-water and then extracted with diethyl ether. The combined ether extract is washed with brine and dried over sodium sulfate. After filtration, the filtrate is concentrated and the residue is distilled in a Kugelrohr to yield 1.6 g (23%) of the product as a light-yellowish oil. 1H NMR (500 MHz, CDCl3, in ppm) δ 4.10 (q, 4H, J=7.5 Hz), 1.99 (s, 4H), 1.24 (t, 6H, J=7.5 Hz), 0.22 (s, 6H).

Workup

  1. temperatureThe flask is then cooled in an ice-water bath
  2. temperaturethe mixture is warmed up to room temperature
  3. stirringstirred overnight
  4. extractionextracted with diethyl ether
  5. extractionThe combined ether extract
  6. washis washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate is concentrated
  10. distillationthe residue is distilled in a Kugelrohr

Sources & evidence

ORD record
ord-274e3d3df4e248f29af0c2063f9bcbb9
Source dataset
uspto-grants-2012_08
Patent number
US08247341B2

Reaction notes

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