Sodium borohydride → 7-({4-[(4-hexylphenyl)ethynyl]anilino}methyl)-2,2-dimethyl-4H-1,3-benzodioxin-4-one

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Reaction Steps

A solution of 2,2-dimethyl-4-oxo-4H-1,3-benzodioxine-7-carbaldehyde (700 mg; 3.38 mmol) and 4-[(4-hexylphenyl)ethynyl]aniline (940 mg; 3.38 mmol) in toluerene (40 mL) was refluxed for 48 hours with azeotropic removal of water. The solvent was removed under reduced pressure and the residue was taken up in a mixture of MeOH (20 mL) and THF (20 mL). NaBH4 (130 mg, 3.38 mmol) was added and the resulting mixture was stirred at rt for 8 hours. The solvents were removed under reduced pressure. The residue was taken up in EtOAc and washed with a saturated aqueous solution of NaACO3 and brine. The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure to give a brown oil. Purification by flash chromatography on silica (EtOAc:c-Hex 1:9 then 1:4) gave 466 mg (30%) of the title compound as a pale yellow oil. HPLC, Rt: 6.1 min (purity: 95.6%). LC/MS, M+(ESI: 468.0, M−(ESI): 466.1.

Provenance & Evidence