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Simple Synthesis of 3-Acetyl-2-norbornanone via Diels-Alder Reaction and Reactivity of its Derivatives
Gottschalk, Franz-Josef,Weyerstahl, Peter
, p. 555 - 565 (2007/10/02)
Cyclopentadiene reacts SnCl4-catalyzed with the readily accessible benzyl ether 1b to give norbornene 2.Benzyl cleavage leads to the diol 3, on the other hand hydrogenation yields the 3-acetonorbornanol 13 which is oxidized and methylated via 6 to 7.The acetyl group of diketone 7 reacts selectively with ylen (-> 8) and orthoformate (-> 9).With methyl lithium however the diol 12 is formed.Selective reaction of the 2-ketogroup of 2 is only possible after protecting the acetyl function in 2 (-> 5 -> 14 -> 10 -> 19).The Grignard reaction of 2 is sterically hindered and leads with methyl or ethyl magnesium halide to 4a or b.The α,β-unsaturated ketones 16 resp. 17a and b are obtained from 4a resp. b via hydrogenation (->15a, b), oxidation (-> 11a, b) and dehydration.
