57816-04-3Relevant articles and documents
An Expeditious Synthesis of 8-Methoxy-1-tetralone
Castillo-Rangel, Norma,Pérez-Díaz, José Oscar H.,Vázquez, Alfredo
, p. 2050 - 2056 (2016/07/06)
8-Methoxy-1-tetralone was synthesized in a concise and efficient manner involving a sequential palladium-mediated cross-coupling reaction (Heck), catalytic hydrogenation, and intramolecular acylation mediated by Eaton's reagent or Lewis acids. The pivotal step in the synthesis was the use of a bromine substituent at the benzenoid C4 position of the intermediate methyl 4-arylbutyric ester to ensure cyclization ortho to the methoxy moiety and obviate cyclization at the para position to the thermodynamically preferred 6-methoxy-1-tetralone, the sole product obtained in the absence of this blocking group.
Reaction of 2-Butenoic Acid Dianion and Its N-(4-Methoxyphenyl)amide with Methoxy-Substituted Arynes
Deshmukh, Abdul Rakeeb,Tran, Long,Biehl, Edward R.
, p. 667 - 670 (2007/10/02)
N-(4-Methoxyphenyl)-1-butenamide dianion (6), generated by the reaction of N-(4-methoxyphenyl)-2-butenamide (3) with LDA or LTMP, undergoes exclusive 4-arylation with various methoxy-substituted arynes 2a-e yielding mixtures consisting of a N-(4-methoxyphenyl)-(E)-4-aryl-3-butenamide (9) (85-90percent) and a N-(4-methoxyphenyl)-(E)-4-aryl-2-butenamide 9' (10-15percent).Under certain conditions, 4,4-diarylated products 12 are also obtained. 2-Butenoic acid dianion (14) also reacts with methoxy-substituted arynes affording predominantly 4-aryl-3-butenoic acids 15 and minor amountsof 4-aryl-2-butenoic acids 15'.The exclusive low temperature (-30 to -40 deg C) 4-addition of arynes to dianion 14 is in contrast to the predominant 2-addition that 14 undergoes with certain aldehydes and ketones at comparable temperatures.The mixtures of 4-arylbutenoic acids 15 and 15' and 4-arylbutenamides 9 and 9' were readily hydrogenated (Pd/C) and esterified (MeOH/H2SO4) to synthetically valuable methyl 4-arylbutanoates 17.
