Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 2-[3-(3-bromophenyl)cyclobutylidene]acetate
반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:11][C:10](=O)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:13][O:14][C:15](=[O:36])[CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCl>[CH3:13][O:14][C:15](=[O:36])[CH:16]=[C:10]1[CH2:11][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH2:9]1참가 물질
4
실험 절차
3-(3-Bromo-phenyl)-cyclobutanone (2.00 g, 8.89 mmol) and Triphenyl-phosphoranylidene acetic acid methyl ester (8.33 g, 24.9 mmol) were dissolved in dichloromethane (30 mL) inside a CEM 80 ml microwave vessel. The solution was irradiated in a CEM Discover™ microwave instrument for 30 minutes at 120° C. Pressure reached a maximum of 180 PSI. Purification by column chromatography (isocratic elution; 10% diethyl ether in hexanes) afforded 2.49 gm of a colorless oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.90-3.00 (m, 1H) 3.02-3.14 (m, 1H) 3.17-3.28 (m, 1H) 3.46-3.58 (m, 1H) 3.62 (s, 3H) 3.63-3.71 (m, 1H) 5.74 (q, J=3.0 Hz, 1H) 7.27-7.35 (m, 2H) 7.39-7.43 (m, 1H) 7.50 (t, J=1.9 Hz, 1H); MS (EI) m/z 280 [M+.].