2,2,6,6-Tetramethyl-3,5-heptanedione → HCID 57894198, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-benzyloxy-1-bromobenzene (14.53 g, 55.2 mmol), 3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester (10.72 g, 55.2 mmol) cesium carbonate (21.59 g, 66.3 mmol), and 2,2,6,6-tetramethyl-3,5-heptanedione (2.54 g, 13.8 mmol) in 1-methyl-2-pyrrolidinone (100 mL) is purged with N2, and then copper (I) chloride (2.73 g, 27.6 mmol) is added. The reaction mixture is heated to 120° C. for 18 hours under N2. The mixture is diluted with water and extracted with Et2O. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using a gradient of 19/1 to 9/1 hexanes/ethyl acetate to afford about 10.54 g (51%) of the titled compound. Rf=0.53 (100% hexanes). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calcd for C24H24O4 376, found 377 (M+1, 100%).

Provenance & Evidence