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. 2010 Aug 27;15(9):5909–5927. doi: 10.3390/molecules15095909

Table 2.

Preparation of benzofuran 19.

graphic file with name molecules-15-05909-i002.jpg
Entry R Ar1 Ar2 19 Yield (%)a
1(a) H C6H5 C6H5 83
2(b) A 3,5-(MeO)2C6H3 C6H5 71
3(c) A 3,5-(MeO)2C6H3 4-(Br)C6H4 0
4(d) A 3,5-(MeO)2C6H3 4-(MeO)C6H4 87
5(e) A 3,5-(MeO)2C6H3 2-furyl 38
6(f) A C6H5 4-(MeO)C6H4 80
7(g) A 3,4,5-(MeO)3C6H2 4-(MeO)C6H4 85
8(h) A 3,4-(MeO)2C6H3 4-(MeO)C6H4 81
9(i) B 3,5-(MeO)2C6H3 4-(MeO)C6H4 85

Reagents and conditions: (a) LiTMP (0.5 M in THF, 5 equiv), THF, 0 °C, 2 h; (b) p-TsOH•H2O (1.0 equiv), CH2Cl2, 23 °C, 1 h. aYields refer to chromatographically and spectroscopically homogeneous material. LiTMP = Lithium 2,2,6,6-tetramethylpiperidide; p-TsOH = toluenesulfonic acid.