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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
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HRID 717516 반응식
[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
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참가 물질

7

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

생성물 1

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

시약·촉매·용매 2

HCID 83717Copper iodide촉매
HCID 8008Butyronitrile용매

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온도
125 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-8b310ce676094eeb89fc4d2a7c35ef7b
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09193714B2

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