摘要：

78939-37-4 ]C 7 H 8 O 5 (MW 172.15) InChI= 1S/C7H8O5/c1-11-6(9)4-3-5(8)7(10)12-2/h3-4H,1-2H3/b4-3+ InChIKey= AMBZDHXNCVCBRQ-ONEGZZNKSA-N (useful reagent for Doebner–von Miller-type annulations, quinoline synthesis; a potential dienophile) Alternate Names: dimethyl 2-oxoglutaconate. Physical Data: mp 61–62°C. Preparative Methods: dimethyl 2-oxoglutaconate ( 1 ) has been known since 1946, when it was prepared in low yield by the oxidation of dimethyl glutaconate . 1 Although the preparation by this route was recently improved, 2 the following procedure, as previously described, has been shown to be a more efficient synthesis. 3 A solution of bromine in dry methylene chloride (1.01 equiv) is added dropwise to a solution of dimethyl 2-oxoglutarate in the same solvent at reflux, followed by removal of solvent (and HBr) in vacuo. The resulting α-bromo ketone is treated with Triethylamine (TEA, 1 equiv) in ether at 25°C for 20 min followed by filtration, passing the filtrate through a pad of silica gel, and concentration in vacuo to provide ( 1 ). Handling, Storage, and Precautions: the enone functional group is remarkably reactive with amines at rt. Care should be exercised to avoid addition of excess TEA in its preparation. Handle in a fume hood.

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