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- A white solid; mp 38–40 °C; 1H NMR (360 MHz, CDCl3) d 7.80 (d, J = 8.3 Hz, 4 H), 7.35 (d, J = 8.3 Hz, 4 H), 4.05 (t, J = 6.6 Hz, 4 H), 2.68 (t, J = 7.3 Hz, 4 H), 2.45 (s, 6 H), 1.75–1.55 (m, 8 H), 1.45–1.15 (m, 28 H); 13C NMR (90 MHz, CDCl3) d 144.57, 133.27, 129.76, 127.84, 70.65, 39.14, 29.38 (C × 2), 29.31(C × 2), 29.17, 28.88, 28.79, 28.47, 25.29, 21.60
- Hobbs , C. F. , McMillin , C. K. , Papadopoulos , E. P. and Vanderwerf , C. A. 1962 . J. Am. Chem. Soc. , 84 : 43
- Heaney , H. and Ley , S. V. 1974 . Org. Synth. , 54 : 58
- Bocchi , V. , Casnati , G. , Dossena , A. and Villani , F. 1976 . Synthesis , : 414
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- General procedure for alkylation: A solution of pyrrole (1.69 g, 25.2 mmol) in HMPA (56 mL) was flushed with nitrogen and cooled to 0 °C. To the solution was added with stirring sodium hydride (538 mg, 22.4 mmol; previously washed with hexane to remove mineral oil) over a period of 10 min. The reaction mixture was stirred at room temperature for 5h and then cooled to 0 °C again. 4 (4.0 g, 5.60 mmol) was added and the resulting mixture was allowed to room temperature and stirred at room temperature for 12 h. The mixture was diluted with water (50 mL) and extracted with diethyl ether (3 × 60 mL). The combined organic layers were washed with water (2 × 50 mL) anddried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure and purified by chromatography on silica gel (80 g, 10:1 hexane/diethyl ether as a eluent) to afford the product as a pale yellow oil (1.73 g, 60%). 1H NMR (360 MHz, CDCl3) d 6.63 (dd, J = 2.1, 2.1 Hz, 4 H), 6.13 (dd, J = 2.1, 2.1 Hz, 4 H), 3.86 (t, J = 7.2 Hz, 4 H), 2.70 (t, J = 7.3 Hz, 4 H), 1.80–1.50 (m, 8 H), 1.50–1.20 (m, 28 H); 13C NMR (90 MHz, CDCl3) d 120.43,107.74, 49.61, 39.19, 31.56, 29.73, 29.45 (C × 2), 29.44, 29.20 (C × 2), 29.19, 28.50, 26.76; Anal. Calcd for C15H26NS: C, 71.37; H, 10.38. found: C, 71.26; H, 10.84
- Wurm , B. D. , Brittain , S. T. and Kim , Y.-T. submitted to Langmuir