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CAS No. : | 7766-50-9 | MDL No. : | MFCD00040825 |
Formula : | C11H21Br | Boiling Point : | No data available |
Linear Structure Formula : | CH2CHCH2CH2CH2CH2CH2CH2CH2CH2CH2Br | InChI Key : | YPLVPFUSXYSHJD-UHFFFAOYSA-N |
M.W : | 233.19 | Pubchem ID : | 284148 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
Magnesium turnings (2.0 g, 83.3 mmol) were covered with anhydrous Et2O (10 mL) and a solution of 1-bromoundecene (5.0 mL, 23.0 mmol) in anhydrous Et2O (15 mL) was added in small aliquots until the reaction begins. The remaining halide solution was added dropwise, then heated to reflux (1 hour), allowed to cool to rt and then added to a cooled solution of the Weinreb amide (2.82 g, 18.2 mmol in 15 mL anhydrous Et2O, 0 C.) via cannula. The resulting slurry was stirred (3 h) and then quenched with equal amounts of 1 N HCl and H2O. After warming to rt the mixture was separated and the aqueous layer was extracted with Et2O (2×). The combined organics were washed with sat'd. NaHCO3, brine, dried (Na2SO4), filtered, and evaporated to yield crude furyl ketone. 1H NMR: δ 7.58 (dd, 1H, 3JH,H=1.7 Hz, 4JH,H=0.74 Hz, H-2), 7.18 (dd, 1H, 3JH,H=3.6 Hz, 4JH,H=0.74 Hz, H-4), 6.53 (dd, 1H, 3JH,H=1.7 Hz, 3JH,H=3.6 Hz, H-3), 5.82 (m, 1H), 5.00 (m, 1H, vinyl), 4.92 (m, 1H, vinyl), 2.82 (t, 2H, 3JH,H=7.5 Hz, H-7), 2.04 (qd, 2H, 3JH,H=7.5 Hz, H-15), 1.72 (quintet, 2H, 3JH,H=7.5 Hz, H-8), 1.37-1.20 (m, 12H). 13C NMR: δ 189.9, 152.9, 146.2, 139.2, 116.8, 114.1, 112.1, 38.5, 33.8, 29.7, 29.4, 29.3, 29.2, 29.1, 28.9, 24.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With potassium carbonate; triethylamine; In N,N-dimethyl-formamide; at 80℃; for 36h; | Step 1: Synthesis of undec-1-eneiminodiacetic acid methyl ester Added to a solution of dimethyliminodiacetate (hydrochloride) (8.53 g; 43 mmol; 1 eq.) dissolved in 250 ml of DMF, were triethylamine (4.35 g; 6 ml; 43 mmol; 1 eq.), 11-bromoundecene (95%) (10.53 g; 9.9 ml; 43 mmol) and potassium carbonate (5.95 g; 43 mmol; 1 eq.). The reaction was heated at 80 C. over 36 hours. After evaporating the DMF and taking up in ethyl acetate, the reaction mixture was washed successively with distilled water (two times) and with a saturated sodium chloride solution and dried over anhydrous magnesium sulphate. The residue was purified by chromatography over silica gel (cyclohexane/ethyl acetate (75/25)) to give a colourless liquid. The characteristics of the product obtained were the following: Mass obtained: 6 g Yield: 84% 1H NMR (200 MHz; CDCl3): 1.28 (12H; m; H6-12); 1.59 (2H; m; H5); 2.03 (2H; m; H12); 3.74 (6H; s; H1); 4.09 (4H; t; H3+4; 3JH-H=6.8 Hz); 4.16 (2H; s; H3); 4.97 (2H; m; H14); 5.81 (1H; m; H16) 13C NMR (200 MHz; CDCl3): 26.14; 29.20; 29.29; 29.48; 29.59; 29.77; 29.84; 34.18; 49.51 (C3); 52.54 (C1); 66.89 (C4); 114.52 (C14); 139.57 (C13); 170.40 (C2). |