Sodium Carbonate → HCID 70172846, compound

Participants

Reaction Steps

2-(Pivaloylamino)phenylboric acid (F. Guiller, F. Nivoliers, A. Godard, F. Marsais, G. Quéguiner, M. A. Siddiqui, V. Snieckus, J. Org. Chem. 1995, 60, 292) (0.66 g, 3.0 mmol), 3-(trifluoromethylsulfonyloxy)-2,5-dihydrofuran-4-carboxylic acid-methyl ester (0.69 g, 2.5 mmol), tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol) and a 2M aqueous Na2CO3 solution (1.26 ml, 2.52 mmol) are refluxed in DME (40 ml) for 2.5 hours. The batch is diluted with ethyl acetate, washed with water and saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with ethyl acetate-hexane yields 0.65 g (87%) of 4-(2-(pivaloylamino)phenyl)-2,5-dihydrofuran-3-carboxylic acid-methyl ester (flash point 105-6° C.). 0.59 g (1.94 mmol) of it is then refluxed in concentrated hydrochloric acid for 2 hours. The batch is poured onto ice and extracted with ethyl acetate and dichloromethane. After drying (Na2SO4) and concentration by evaporation, the residue is heated for two more hours with concentrated HCl and worked up as described: 0.22 g (58%) of product.

Provenance & Evidence