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Sodium hydride → HCID 11175089, 화합물

HRID 2424185
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HRID 2424185 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[C:9]([OH:11])[CH:10]=1.C([O:28][C:29]1[CH:34]=[CH:33][C:32](Br)=[CH:31][CH:30]=1)C1C=CC=CC=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[C:9]([CH:10]=1)[O:11][C:32]1[CH:33]=[CH:34][C:29]([OH:28])=[CH:30][CH:31]=1
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참가 물질

8

반응물 4

HCID 24758Sodium hydrideHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 11736683HCID 11736683, 화합물

생성물 1

HCID 11175089HCID 11175089, 화합물수율 20.9%

시약·촉매·용매 3

HCID 167845
palladium(II) acetate
촉매
HCID 962Water용매
HCID 1140Toluene용매

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온도
90 °C

실험 절차

The title compound was synthesized by referring to J. Am. Chem. Soc., 1999, 121 (18), 4369. To a suspension of 60% sodium hydride (600 mg) in toluene (50 ml) was added 5-methoxy-2-(3-methoxybenzyl)phenol (2.4 g), and the solution was stirred at 90° C. until generation of gas was stopped. The reaction solution was cooled to room temperature, then 1-benzyloxy-4-bromobenzene (2.6 g), palladium(II) acetate (112 mg), 2-(di-tert-butylphosphino)biphenyl (149 mg) were sequentially added thereto, and the solution was stirred for 18 hours and 50 minutes at 95° C. To the reaction solution was added water, the solution was extracted with ethyl acetate, then the insoluble material was filtered through celite pad, the filtrate was dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. Obtained by purifying the residue by silica gel column chromatography (hexane-ethyl acetate system), 2-(4-benzyloxy phenoxy)-4-methoxy-1-(3-methoxybenzyl)benzene (1.4 g) was used according to an analogous synthetic method to Example 22 to provide the title compound (690 mg).

후처리

  1. customThe title compound was synthesized
  2. temperatureThe reaction solution was cooled to room temperature
  3. stirringthe solution was stirred for 18 hours and 50 minutes at 95° C
  4. extractionthe solution was extracted with ethyl acetate
  5. filtrationthe insoluble material was filtered through celite pad
  6. dry with materialthe filtrate was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customObtained
  9. customby purifying the residue by silica gel column chromatography (hexane-ethyl acetate system), 2-(4-benzyloxy phenoxy)-4-methoxy-1-(3-methoxybenzyl)benzene (1.4 g)

출처 및 근거

ORD 기록
ord-38b44a276e46466da7419624c24f7920
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960412B2

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