Water → HCID 23147317, compound

HRID 495298Notes

Reaction equation

HRID 495298 reaction equation
[OH:1][C:2]1[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CC(C)=O>[CH2:26]([O:1][C:2]1[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:6]([O:8][CH2:14][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)[CH:7]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11230647HCID 11230647, compound

Product 1

HCID 23147317HCID 23147317, compoundYield 168.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 1 (1.81 g, 7.00 mmol) obtained in Example 1 was dissolved in acetone (50 mL), and potassium carbonate (5.88 g, 42.6 mmol) and benzyl bromide (3.33 mL, 28.0 mmol) were added thereto and stirred with heating under reflux for 1.5 hours. Water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The residue was purified through silica gel column chromatography (n-hexane/ethyl acetate=20/1 to 9/1) to obtain methyl 3,5-bis(benzyloxy)-2-phenylphenylacetate (2.58 g, 84%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1.5 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (n-hexane/ethyl acetate=20/1 to 9/1)

Sources & evidence

ORD record
ord-6fe1cbb2c4674d459184bb3d9e698770
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

Loading…