反应详情

温度

18 °C

DCC (1.60 g, 7.75 mmol) was added to a solution of 2-iodoacetic acid (1.44 g, 7.74 mmol), 2-[(4-isopropoxy-3-methoxy-phenyl)ethynyl]-5-isopropoxy-4-methoxyphenol (2.6 g, 7.03 mmol)and DMAP (43 mg, 0.35 mmol) in CH2Cl2 (30 mL) and the solution thereby obtained was stirred at 18° C. for 3 h. The resulting suspension was filtered (CH2Cl2 rinse) and the filtrate concentrated under reduced pressure. The residue was suspended in ether (30 mL) at 0° C. with rapid stirring then filtered [rinsing with Et2O (20 mL) pre-cooled at 0° C.] giving the title compound (3.67 g, 97%) as a cream solid mp 127-8° C. IR (KBr disc, cm−1) 2969, 2930, 2833, 1755, 1611, 1575, 1516, 1467, 1416, 1402, 1385, 1365, 1320, 1252, 1236, 1212, 1135, 1108. 1H NMR (300 MHz, CDCl3) δ 7.08 (dd, J=1.8, 8.4 Hz, 1H), 7.04 (d, J=2.1 Hz, 1H), 7.01 (s, 1H), 6.82 (d, J=8.4 Hz, 1H), 6.65 (s, 1H), 4.53 (septet, J=6.0 Hz, 2 Hz), 3.95 (s, 2H), 3.85 (s, 6H), 1.38 (d, J=6.0 Hz, 6H), 1.37 (d, J=6.0 Hz, 6H). 13C NMR+APT (75.5 MHz, CDCl3) δ 167.3 (C), 150.0 (C), 148.4 (C), 148.3 (C), 148.2 (C), 145.1 (C), 125.2 (CH), 115.6 (C), 115.3 (CH), 115.2 (CH), 115.0 (CH), 108.8 (CH), 93.6 (C), 82.7 (C), 72.0 (CH), 71.6 (CH), 56.5 (CH3), 56.3 (CH3), 22.3 (CH3), 22.0 (CH3), −6.2 (CH2). MS (70 eV) m/z (%): 538 (80, M+·), 496 (10, M+·-CH2CHCH3), 370 (10, M+·-CH2ICO), 328 (34), 286 (100); HRMS calcd for C24H27O6I 538.0852. Found 538.0854.

1. customthe solution thereby obtained
2. filtrationThe resulting suspension was filtered
3. wash(CH2Cl2 rinse)
4. concentrationthe filtrate concentrated under reduced pressure
5. customwas suspended in ether (30 mL) at 0° C.
6. stirringwith rapid stirring
7. filtrationthen filtered
8. wash[rinsing with Et2O (20 mL) pre-cooled at 0° C.]