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CAS No. : | 21834-92-4 | MDL No. : | MFCD00036615 |
Formula : | C13H16O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 188.27 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylsilane; bismuth(III) bromide; In acetonitrile; for 1.3h; | Step 1: trans-2-[4-(5-Methyl-2-phenyl-hex-2-enyloxy)-cyclohexyl]-isoindole-1,3-dione To a stirred mixture of 1 g of trans-2-(4-(tert-butyl-dimethyl-silyloxy-cyclohexyl)-isoindole-1,3-dione, 20 mL of anhydrous acetonitrile, 0.8 mL of triethylsilane and 0.6 g of <strong>[21834-92-4]5-methyl-2-phenyl-2-hexenal</strong> (commercial, predominantly trans was added) 0.08 g of bismuth tribromide. After stirring for 1.3 h, the reaction was quenched with 10 mL of saturated sodium bicarbonate and extracted with 3*25 mL portions of ethyl acetate. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Chromatography over silica gel eluding with a gradient of 1%-20% ethyl acetate in hexane gave first 0.30 g of saturated product, trans-2-[4-(5-methyl-2-phenyl-hexyloxy)-cyclohexyl]-isoindole-1,3-dione, then 0.50 g of product as a resin: 1H NMR (400 MHz, CDCl3) 7.8 (m, 2H), 7.7 (m, 2H), 7.3-7.1 (m, 5H), 5.8 (t, 1H), 4.25 (s, 2H), 4.15 (m, 2H), 3.4 (m, 1H), 2.3 (m, 2H), 2.1 (d, 2H), 1.9 (t, 2H), 1.75 (d, 2H), 1.65 (m, 1H), 1.35 (m, 2H), 1.3 (t, 2H), 0.9 (d, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In ethanol; dichloromethane; water; | EXAMPLE 11 (R)-1-(2-((((5-Methyl-2-phenyl-2-hexen-1-ylidene)amino)oxy)ethyl)-3-piperidinecarboxy acid hydrochloride To a solution of <strong>[21834-92-4]5-methyl-2-phenyl-2-hexenal</strong> (5.0 g, 27 mmol) and hydroxylammonium chloride (3.7 g, 53 mmol) in a mixture of 96% ethanol (20 ml) and water (5 ml) was carefully added a solution of sodium carbonate (11.2 g, 106 mmol) in water (30 ml). The resulting mixture was stirred for 2h, the precipitated compound was filtered off and suspended in dichloromethane (500 ml). The suspension was filtered and the solvent evaporated from the filtrate in vacuo to give 4.1 g of <strong>[21834-92-4]5-methyl-2-phenyl-2-hexenal</strong> oxime. |
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