Pyrrole → (E)-1-[2-(Biphenyl-4-yloxyl)vinyl]-1H pyrrole

HRID 1053508

反応式

HRID 1053508 の反応式
I/[CH:2]=[CH:3]/[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[NH:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1.C([O-])([O-])=O.[Cs+].[Cs+]>[Cu]I>[C:8]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:10][C:5]([O:4]/[CH:3]=[CH:2]/[N:17]2[CH:21]=[CH:20][CH:19]=[CH:18]2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8027PyrroleHCID 10796Cesium carbonateHCID 89873752(E)-4-((2-Iodovinyl)oxy)-1,1'-biphenyl

生成物 1

HCID 89873682(E)-1-[2-(Biphenyl-4-yloxyl)vinyl]-1H pyrrole収率 86.4%

試薬・触媒・溶媒 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒

実験手順

The compound 10 was prepared following the procedure described for 5 with 4 (0.2 g, 0.62 mmol, 1 eq), pyrrole (0.062 g, 0.93 mmol, 1.5 eq), Cs2CO3 (0.40 g, 1.2 mmol, 2.5 eq), CuI (0.059 g, 0.31 mmol, 0.5 eq) and L2 (0.060 g, 0.31 mmol, 0.5 eq) at 70° C. for 12 h to give crude product which were purified by silica gel column chromatography using ethyl acetate-hexane (9:95) to afford compound 10 as white crystals (0.14 g, 85%): mp 102-105° C. Olefinic protons coupling on the named compound gave an AB-system with a typical roof effect with peaks centered at 7.04 and 6.99 ppm. 1H NMR (300 MHz, CDCl3): 7.62-7.53 (m, 4H, HAr), 7.48-7.40 (m, 2H, HAr), 7.38-7.31 (m, 1H, HAr), 7.17-7.09 (m, 2H, HAr), 7.04 (distorted d, 1H, J=11.1 Hz, (O)—CH═CH(N)), 6.99 (distorted d, 1H, J=11.1 Hz, (O)—CH═CH(N)), 6.82 (dd, 2H, J1=4.2 Hz, J2=2.2 Hz, CH═CH of pyrrole), 6.28 (dd, 2H, J1=4.2 Hz, J2=2.2 Hz, CH═CH); 13C NMR (75 MHz, CDCl3): 156.8, 140.4, 136.3, 135.0, 128.8, 128.4, 127.1, 126.9, 119.6, 118.3, 116.5, 110.0 ppm; IR (cm−1): 3086, 3034, 2715, 2682, 1659, 1607, 1587, 1517, 1485, 1360, 1326, 1300, 1239, 1229, 1185, 1173, 1119, 1094, 1072, 1056, 1007, 975, 907, 857, 838, 614; HRMS (ESI) Calculated for C18H15NO [M+H]+ 262.1232. Found 262.1233; Elemental analysis calculated for C18H15NO.0.17H2O: C, 81.77; H, 5.85; N, 5.29. found: C, 81.76; H, 5.91; N, 5.03.

後処理

  1. customThe compound 10 was prepared
  2. customto give crude product which
  3. customwere purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b7a2a21cfa5d4804b1104aa5508ab2db
出典データセット
uspto-grants-2016_07
特許番号
US09393306B2

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