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Ethylene Glycol → 2-(4-((5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)methyl)phenoxy)ethanol

HRID 717516
ノート
印刷プレビュー

反応式

HRID 717516 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=1)[C:13]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:28][CH:27]=1)=[C:12]2[CH3:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:41]([OH:44])[CH2:42][OH:43].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)CCC.[Cu](I)I>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:43][CH2:42][CH2:41][OH:44])=[CH:21][CH:20]=1)[C:13]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:28][CH:27]=1)=[C:12]2[CH3:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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

7

反応物 4

HCID 174Ethylene GlycolHCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 120740765-(Benzyloxy)-2-(4-(benzyloxy)phenyl)-1-(4-iodobenzyl)-3-methyl-1H-indole

生成物 1

HCID 121331372-(4-((5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)methyl)phenoxy)ethanol収率 61.5%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒
HCID 8008Butyronitrile溶媒

反応条件

温度
125 °C

実験手順

A mixture of 5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-1-(4-iodobenzyl)-3-methyl-1H-indole (1.01 g, 1.58 mmol), ethylene glycol (0.44 mL, 7.89 mmol), copper iodide (32 mg, 0.17 mmol), 1,10-phenanthroline (60 mg, 0.33 mmol), and potassium carbonate (436 mg, 3.15 mmol) in butyronitrile (3 mL) was degassed with three vacuum/N2 cycles. The reaction was heated at 125° C. for 26 hrs and upon completion, allowed to cool to room temperature. It was then diluted with water. The aqueous layer was extracted three times with ethyl acetate. The combined ethyl acetate extracts were washed with water (40 mL) and brine (40 mL), dried (MgSO4), filtered, concentrated and purified by silica gel chromatography (0%-40% ethyl acetate in hexanes) to give 554 mg of 2-(4-((5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indol-1-yl)methyl)phenoxy)ethanol as a pale yellow foam. 1H NMR (400 MHz, DMSO-d6): δ 7.48 (d, 4H), 7.45-7.37 (m, 4H), 7.37-7.32 (m, 2H), 7.30 (d, 2H), 7.21 (d, 1H), 7.15-7.10 (m, 3H), 6.81 (dd, 1H), 6.74 (s, 4H), 5.20-5.10 (m, 6H), 4.81 (t, 1H), 3.87 (t, 2H), 3.64 (q, 2H), 2.16 (s, 3H). LCMS: 570.0 (M+H)+.

後処理

  1. customwas degassed with three vacuum/N2 cycles
  2. temperatureto cool to room temperature
  3. additionIt was then diluted with water
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. washThe combined ethyl acetate extracts were washed with water (40 mL) and brine (40 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography (0%-40% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-8b310ce676094eeb89fc4d2a7c35ef7b
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09193714B2

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