Hexane → 2-Ethyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide

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Reaction Steps

2-Ethyl-benzofuran-3-carbonyl chloride, prepared in step 2 of Example 21, in 50 mL of anhydrous THF was added under nitrogen dropwise over 1 h to a suspension of 6-methylaminomethyl-naphthalen-2-ol (1.48 g, 7.9 mmol), prepared in the previous step, and triethylamine (1.1 mL, 7.9 mmol) in 150 mL anhydrous THF at room temperature. The reaction stirred at room temperature for 20 h (overnight). The solid present was removed by filtration and the filtrate concentrated under reduced pressure to give a brown foam. The foam was dissolved in ethyl acetate and extracted with 1N HCl. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give a brown oil which solidified when treated with hexane. The crystals were triturated with hexane and dried under reduced pressure to give 2-ethyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (2.38 g, 84%) as tan solid, mp 80-90° C.

Provenance & Evidence