2-acetyl-5-chlorophenyl methyl

Acetyl-5-chlorophenyl Methyl Tellurium1 To a well-stirred solution of 9.17 g (50 mmol) of 4-chloro-/V,/V-dimethylbenzamide in 50 ml dry tetrahydrofuran at 0° is added dropwise a solution containing 55 mmol methyl lithium. The stirred mixture is kept at 0° for 2h. Then a solution of 8.7 g (11.3 m/, 75 mmol) of 1,2-bis[JV,JV-dimethylamino]ethane in 20 ml dry tetrahydrofuran is added. 47 ml of a 1.6 molar solution of butyl lithium (75 mmol) in hexane are added dropwise. The mixture is kept at 0° overnight and then a solution of 14.3 g (50 mmol) of dimethyl ditcllurium in 20 ml of dry tetrahydrofuran is added. The mixture is stirred for 6 h and then hydrolyzed and worked up in the usual way yield 30% m.p. 117 (hexane). 

The nucleophilic reactivity of the oxygen has been observed in acetylation by acetic anhydride of 2-aryl- and 2-heteroaryl-A-2-thiazoline-4-ones (181) (388, 397, 410, 414, 416, 419, 422, 426. 427) and methylation of 5-(4 -chlorophenyl)-A-2-thiazoline-4-one (416) (Scheme 94). 

The Knoevenagel and Wittig type reactions have been used for the creation of the 6-bond. The condensation of octadecanal with methyl p-(chlorophenyl)sulfinyl acetate in the presence of piperidine afforded the corresponding acetate after acetylation of the hydroxy group which, after subsequent molibdenum-catalyzed elimination, gives the dienic ester as a 4 1 E,E E,Z mixture. After final amidation, the amide trichonine (13) [40] is obtained (Scheme 2). A similar strategy has been used for the synthesis of piperovatine (21) with total E,E-stereoselectivity [41]. 

C15H22N2O9, (3SR,4RS,5SR)-2-Acetyl-5-(methoxycarbonylmethyl)-1-methyl-3,4, 5-tr is (methoxycarbonyl )pyrazoline, 45B, 211 ClsHi2N2O, 4-Benzylidene-2-phenyl-2-imidazoline-5-one, 46B, 212 Cl gHi 3CI2N3O CH, 0, rac-2-Methylamino-4,5-bis(p-chlorophenyl)-4-hydroxy-4H-imidazole methanol solvate, 45B, 212 ClgHi N202, 5-Benzyl-5-hydroxy-2-phenyl-imidazolin-4-one, 45B, 213 Cl gHi iiN2S2, 1, 3-Diphenylimidazolinium-2-dithiocarboxylate, 46B, 212 CiGHi5BrN20, 2-(1-Imidazolin-2-yl)benzophenone hydrobromide, 33B,... 

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