Sodium hydride → HCID 11175089, compound

HRID 1950614Notes

Reaction equation

HRID 1950614 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 11175089HCID 11175089, compoundYield 20.9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-dbde0189349b4acebfe4acd4d4c9f194
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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