[NH2:1][C:2]1[C:10]2[O:9][C:8]3[CH2:11][CH2:12][CH2:13][CH2:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16](=O)[CH2:17][CH2:18][C:19](=O)[CH3:20].O.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[CH3:20][C:19]1[N:1]([C:2]2[C:10]3[O:9][C:8]4[CH2:11][CH2:12][CH2:13][CH2:14][C:7]=4[C:6]=3[CH:5]=[CH:4][CH:3]=2)[C:16]([CH3:15])=[CH:17][CH:18]=1
A mixture of 6-amino-1,2,3,4-tetrahydrodibenzofuran (230 mg), 2,5-hexanedione (145 mg) and conc. hydrochloric acid (1 drop) in ethanol (3 ml) was refluxed for 1 hour and poured into water. The mixture was neutralized with aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from a mixture of ethanol and water to give 6-(2,5-dimethylpyrol-1-yl)-1,2,3,4-tetrahydrodibenzofuran (235 mg).
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