4-Fluoroaniline → HCID 68154261、化合物

反応式

[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C[Al](C)C.[O:13]1[C@@:23]23[C@H:18]([CH2:19][CH2:20][O:21][CH2:22]2)[CH2:17][CH2:16][CH2:15][CH:14]13>C(Cl)Cl>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C@H:14]2[C@:23]3([OH:13])[C@H:18]([CH2:19][CH2:20][O:21][CH2:22]3)[CH2:17][CH2:16][CH2:15]2)=[CH:4][CH:3]=1

参加物

実験手順

To a mixture of 4-fluoroaniline (0.721 g, 6.48 mmol) in CH2Cl2 (6 mL) at 0° C. was added trimethylaluminum (2M in toluene, 3.24 mL) dropwise. The mixture was warmed and stirred to rt for 30 min. (1aS,5aS)-hexahydro-4H-oxireno[i]isochromene (0.200 g, 1.30 mmol) in CH2Cl2 2 mL+0.5 mL rinse) was then added and the mixture was stirred at rt overnight. The reaction was cooled to 0° C. and treated with 50% NaOH (1 mL) then water (1 mL) The mixture was diluted with more water and extracted 3× with CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 6.84-6.90 (m, 2H), 6.51-6.57 (m, 2H), 3.90-3.97 (m, 1H), 3.50-3.64 (m, 3H), 3.35-3.45 (m, 2H), 2.61 (s, 1H), 1.95-2.04 (m, 1H), 1.32-1.75 (m, 8H). HRMS (ES) m/z M+H cal'd: 266.1551. found: 266.1548.