Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Dimethylsilanediyl bis(trifluoromethanesulfonate) | HCID 11121822 | — |
| Product | HCID 59545178 | HCID 59545178 | 23% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08247341B2 |
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| Source dataset | uspto-grants-2012_08 |
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| ORD ID | ord-274e3d3df4e248f29af0c2063f9bcbb9 |
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| Source note | uspto-grants-2012_08 |
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