4-Methoxyphenol → (E)-4-[2-(4-Methoxyphenoxy)vinyloxy]biphenyl

HRID 1053505

反応式

C(C1C=CC(O/C=C/OC2C=CC(C3C=CC=CC=3)=CC=2)=CC=1)(C)(C)C.I/[CH:28]=[CH:29]/[O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:33][CH:32]=1.[CH3:43][O:44][C:45]1[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=1.C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I>[CH3:43][O:44][C:45]1[CH:50]=[CH:49][C:48]([O:51]/[CH:28]=[CH:29]/[O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:33][CH:32]=2)=[CH:47][CH:46]=1

参加物

反応条件

温度: 80 °C

実験手順

Compound 7 was prepared according to the general method described for compound 6 above, employing 4 (0.2 g, 0.62 mmol, 1 eq) and 4-methoxyphenol (0.077 g, 0.62 mmol, 1 eq), Cs2CO3 (0.50 g, 1.6 mmol, 2.5 eq), CuI (0.59 g, 0.31 mmol, 0.5 eq) and L1 (0.057 g, 0.31 mmol, 0.5 eq) heating the reaction mixture at 80° C. for 48 h to furnish the crude product which was purified by column chromatography using hexane as the eluent to afford 7 as white crystals (40 mg, 40%): mp 112-115° C. 1H NMR (300 MHz, CDCl3): 7.61-7.52 (m, 4H, HAr), 7.47-7.40 (m, 2H, HAr), 7.36-7.30 (m, 1H, HAr), 7.10 (d, 2H, J=8.6 Hz), 7.00 (d, 2H, J=9.0 Hz), 6.91-6.84 (m, 4H, HAr and HC(O)═C(O)H), 3.80 (s, 3H, —CH3) ppm. 13C NMR (75 MHz, CDCl3): 156.3, 154.3, 150.5, 139.5, 135.6, 135.1, 132.7, 131.4, 129.0, 127.8, 127.3, 125.8, 116.1, 115.0, 113.8, 54.7 ppm; IR (cm−1): 3059, 1658, 1605, 1517, 1485, 1420, 1319, 1264, 1226, 1173, 1122, 896, 838, 737, 639; HRMS (ESI), Calculated for C21H18O3 [M−H]− 317.1178. Found 317.1158; HPLC analysis: 92% purity.

後処理

customto furnish the crude product which

出典と根拠

ORDレコード: ord-7c1f6d6356454f05914d519c43bc617c
出典データセット: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09393306B2

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

関連ノート