Water → HCID 23147624, compound

HRID 495290Notes

Reaction equation

HRID 495290 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([CH2:25][CH2:26][O:27][CH3:28])=[C:10]([C:22](=[O:24])[CH3:23])[C:11]([O:18][CH2:19][O:20][CH3:21])=[CH:12][C:13]=2[O:14][CH2:15][O:16][CH3:17])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:35](Br)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.O>CN(C)C=O>[CH2:35]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([CH2:25][CH2:26][O:27][CH3:28])=[C:10]([C:22](=[O:24])[CH3:23])[C:11]([O:18][CH2:19][O:20][CH3:21])=[CH:12][C:13]=2[O:14][CH2:15][O:16][CH3:17])[CH:5]=[CH:6][CH:7]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 23147383HCID 23147383, compound

Product 1

HCID 23147624HCID 23147624, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[3-(3-hydroxyphenyl)-2-(2-methoxyethyl)-4,6-bis(methoxymethoxy)phenyl]ethanone (25 mg, 0.064 mmol) obtained in Example 134 was dissolved in N,N-dimethylformamide (1.0 mL), and potassium carbonate (35 mg, 0.25 mmol) and benzyl bromide (0.02 mL, 0.17 mmol) were added thereto and stirred at room temperature for 1 hour. Water was added to the reaction solution, and extracted twice with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through silica gel column chromatography (ethyl acetate/n-hexane=1/4 to 1/2) to obtain 1-[3-(3-benzyloxyphenyl)-2-(2-methoxyethyl)-4,6-bis(methoxymethoxy)phenyl]ethanone (30 mg, 97%).

Workup

  1. extractionextracted twice with diethyl ether
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated away under reduced pressure
  4. customThe resulting residue was purified through silica gel column chromatography (ethyl acetate/n-hexane=1/4 to 1/2)

Sources & evidence

ORD record
ord-f4ca0f6e52d549dea946a92556fb28cb
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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