Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl vinyl ether | HCID 8023 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | 8,16,25-Tris(benzenesulfonyl)-2,6,10,14,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaene-9,24-diol | HCID 86637460 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-Ethoxyethyl ether | HCID 10464631 | 168% |
Reaction Steps
To a stirred solution of the C40 diol compound (L) (1.00 g, 1.00 mmol) in CH2Cl2 (10 mL) at 0° C. were added ethyl vinyl ether (0.80 mL, 8.00 mmol) and pyridinium p-toluenesulfonate (0.13 g, 0.50 mmol). The mixture was stirred at 0° C. for 1 h, and warmed to and stirred at room temperature for 14 h. The mixture was then diluted with CH2Cl2 (30 mL), washed with saturated NaHCO3 (10 mL×3), dried over anhydrous K CO3, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel (deactivated by Et3N) column chromatography to give the bis(1-ethoxyethyl)ether (M-3) (1.09 g, 0.84 mmol) in 95% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07928266B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-a431ad9842ef448fb060c9cc79f49b18 |
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| Source note | uspto-grants-2011_04 |
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