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CAS No. : | 693-67-4 | MDL No. : | MFCD00000223 |
Formula : | C11H23Br | Boiling Point : | - |
Linear Structure Formula : | CH3(CH2)10Br | InChI Key : | IKPSIIAXIDAQLG-UHFFFAOYSA-N |
M.W : | 235.20 | Pubchem ID : | 12744 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P304+P340-P305+P351+P338-P405 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | 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 |
---|---|---|
82.8% | Magnesium turnings (21.6 g, 0.901 mol, 3.7 eq/halide) were covered with anhydrous Et2O (150 mL) and a solution of 1-bromoundecane (54.0 mL, 0.242 mol) in anhydrous Et2O (200 mL) was added in small aliquots until the reaction begins. The remaining bromoundecane 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 (30.0 g, 0.194 mol in 200 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, which was distilled under vacuum (b.p. 131-138 C., 0.2 mm Hg) to give pure furyl ketone (40.2 g, 0.161 mol, Yld. 82.8%). 1H NMR: δ 7.55 (m, 1H, H-2), 7.15 (d, 1H, 3JH,H=3.6 Hz, H-4), 6.50 (dd, 1H, 3JH,H=1.7 Hz, 3JH,H=3.6 Hz, H-3), 2.78 (t, 2H, 3JH,H=7.5 Hz, H-7), 1.69 (quintet, 2H, 3JH,H=7.4 Hz, H-8), 1.34-1.23 (m, 16H), 0.90 (t, 3H, 3JH,H=7.1, CH3). 13C NMR: δ 190.1, 153.3, 146.5, 117.1, 112.5, 38.9, 32.3, 30.1, 30.0, 29.9, 29.8, 29.7, 24.7, 23.0, 14.5. |