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1-Iodo-4-octylbenzene → HCID 86660604、化合物

HRID 2046036
ノート
印刷プレビュー

反応式

HRID 2046036 の反応式
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(O[N:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1)(=O)C1C=CC=CC=1>C1COCC1.CCOCC.[Cl-].[Cl-].[Zn+2]>[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([N:25]2[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:30]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 115948361-Iodo-4-octylbenzeneHCID 20294525HCID 20294525、化合物

生成物 1

HCID 86660604HCID 86660604、化合物収率 31.4%

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒4 回

反応条件

温度
0 °C

実験手順

To a solution of the product of Step A (0.32 g; 1.01 mmol) in anhydrous THF (2 ml) 2 M iPrMgCl in THF (0.56 ml; 1.11 mmol) was added at −15° C. under N2, followed 1.27 M solution of anhydrous ZnCl2 in THF (0.41 ml; 0.52 mmol), after stirring for 1 h at 0° C. The resulting mixture was stirred for 30 min on ice-bath under N2 and the solution of the product of Step B (0.16 g; 0.51 mmol) and CuCl2 (2.5 mol %) in anhydrous THF (10 ml) was added. The resulting mixture was allowed to warm up to room temperature and stirred for additional 10 min. This was diluted to 20 ml with Et2O and washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane/EtOAc 9:1) to give the title compound (0.06 g; 31%), as a creamy syrup. 1H-NMR (CDCl3) 7.07 (d, 2H, J=8.6 Hz); 6.84 (d, 2H, J=8.6 Hz); 3.55 (t, 4H, J=5 Hz); 3.06 (t, 4H, J=5 Hz); 2.51 (t, 2H, J=7.94 Hz); 1.55-1.38 (m, 11H); 1.26 (m, 10H); 0.86 (t, 3H, J=6.93 Hz).

後処理

  1. stirringThe resulting mixture was stirred for 30 min on ice-bath under N2
  2. temperatureto warm up to room temperature
  3. stirringstirred for additional 10 min
  4. washwashed with 5% NaHCO3, H2O, brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customthe residue was purified by FCC (SiO2, hexane/EtOAc 9:1)

出典と根拠

ORDレコード
ord-20265569501a4cb1a853190856a751ca
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08592399B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート