4-Methyl-1-naphthol → 2,6-Dimethyl-2-morpholinophenylbenzochromene

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[O:1]1[CH2:6][CH2:5][N:4](C2C=CC(C(O)(C#C)C)=CC=2)[CH2:3][CH2:2]1.[CH3:18][C:19]1[C:28]2[C:23](=[CH:24]C=CC=2)[C:22](O)=[CH:21][CH:20]=1.[O:30]1[C:39]2[C:34](=[CH:35][CH:36]=[C:37]3[CH:43]=[CH:42][CH:41]=[CH:40][C:38]3=2)[CH:33]=[CH:32][CH2:31]1>C1(C)C=CC=CC=1>[CH3:24][C:23]1([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:22]=[CH:21][CH:20]=[C:19]([CH3:18])[CH:28]1[CH:31]1[CH:32]=[CH:33][C:34]2[C:39](=[C:38]3[CH:40]=[CH:41][CH:42]=[CH:43][C:37]3=[CH:36][CH:35]=2)[O:30]1

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실험 절차

2-p-Morpholinophenylpropargyl alcohol (3C) (8 g) and 4-methyl-1-naphthol (5 g) were dissolved in hot toluene (300 cm3) and the solution added to dry acidic alumina (200 g) in a flask fitted with a condenser. The mixture was heated (20 minutes) on a water bath, cooled and filtered. The residual alumina was extracted with chloroform (3×100 cm3). The combined organic filtrates and extracts were evaporated and the residual oil was purified by chromatography on acidic alumina (100 g) using a 1:20 mixture of dichloromethane and petroleum as eluant. The heliochromic fraction was separated and the solvent removed, leaving a dark brown oil. Two further chromatographic separations failed to improve the quality of the benzochromene (3D; R=Me). The brown oil darkens in air but its n.m.r. spectrum indicates less than 5% impurities.