Alternatived Products of [ 883554-11-8 ]
Product Details of [ 883554-11-8 ]
| CAS No. : | 883554-11-8 |
MDL No. : | MFCD26388566 |
| Formula : |
C14H28O6
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | JUINYDFUOXIVCX-UHFFFAOYSA-N |
| M.W : |
292.37
|
Pubchem ID : | 44622260 |
| Synonyms : |
|
Chemical Name : | tert-Butyl 2,5,8,11-tetraoxatetradecan-14-oate |
Safety of [ 883554-11-8 ]
Application In Synthesis of [ 883554-11-8 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Downstream synthetic route of [ 883554-11-8 ]
- 1
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[ 112-35-6 ]
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[ 1663-39-4 ]
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[ 883554-11-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 75.3% |
With sodium methylate at 20℃; |
1
Example 1 Preparation of tert-butyl-2,5,8,11-tetraoxatetradecan-14-oate Triethyleneglycol monomethyl ether (50 g, 304.5 mmol) was taken in tert-butyl acrylate (35.1 g, 274 mmol) and the mixture was stirred for 10 minutes. Sodium methoxide (1.97 g, 36.5 mmol) was added and stirred at ambient temperature for 8-10 hours. The reaction completion was checked by thin layer chromatography (TLC). The reaction mixture was diluted with ethyl acetate (200 mL) and the organic layer was washed with water, saturated brine solution and dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain tert-butyl 2,5,8,11-tetraoxatetradecan-14-oate (67 g, 75.3%). |
| 65% |
Stage #1: triethylene glucol monomethyl ether With sodium In tetrahydrofuran at 20 - 50℃; Inert atmosphere;
Stage #2: tert-Butyl acrylate In tetrahydrofuran at 20 - 40℃; |
Compound 4: tert-butyl 2,5,8,11 -tetraoxatetradecan-14-oate
Under argon, a mixture of triethylene glycol monomethyl ether (CAS number [112-35- 6], 3 g, 17.36 mmol) and sodium (3.99 mg, 173.57 pmol) in THE (9 mL) was stirred for 2 h at 5000 then overnight at RT. At this time, tert-butyl acrylate (3.08 ml, 20.83 mmol) was added, stirred for 2 h at 40°C then overnight at RT. After that, thereaction medium was concentrated in vacuo, then diluted H20 and extrated with EtOAc. The combined organic phases were washed with brine, dried over MgSO4, filtered, concentrated in vacuo and purified by flash chromatography on 90 g of silica gel (gradient elution heptane/EtOAc) to give 3.3 g of compound 4 (65%). |
|
With hydrogenchloride In tetrahydrofuran |
4 tert-Butyl 3-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}propionate
tert-Butyl 3-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}propionate Triethylene glycol monomethyl ether (1.0 g, 6.1 mmol) and tert-butyl acrylate (390 mg, 3.05 mmol) were dissolved in dry THF and sodium metal (0.7 mg, 0.03 mmol) was added at room temperature. The mixture was stirred for 4 hours and 1 M HCl was added to quench the reaction. The mixture was extracted twice with dichloromethane, and the organic phase was dried over MgSO4 and concentrated in vacuo to provide an oil, which was purified by silica chromatography using ethyl acetate as eluent. The product was an oil, 773 mg (44%). LCMS m=237.1 (M-tBu) |
| 374 mg |
Stage #1: triethylene glucol monomethyl ether With sodium In tetrahydrofuran for 0.5h; Inert atmosphere;
Stage #2: tert-Butyl acrylate In tetrahydrofuran for 1.5h; Inert atmosphere; |
|
Reference：
[1]Current Patent Assignee: BIOCON LIMITED - US2011/118480, 2011, A1
Location in patent: Page/Page column 4
[2]Current Patent Assignee: SANOFI - WO2018/206635, 2018, A1
Location in patent: Page/Page column 165; 166
[3]Current Patent Assignee: NOVO NORDISK A/S - US2010/216691, 2010, A1
[4]Adamson, Christopher; Kajino, Hidetoshi; Kanai, Motomu; Kawashima, Shigehiro A.; Yamatsugu, Kenzo
[Journal of the American Chemical Society, 2021, vol. 143, # 37, p. 14976 - 14980]
- 2
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[ 883554-11-8 ]
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[ 622405-78-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid; water / 2 h / 80 °C
2: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 0 - 45 °C
3: triethylamine / dichloromethane / 0 - 20 °C |
|
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