Cesium carbonate → Methyl 2-(3-formylphenyl)-3,5-bis(methoxymethoxy)phenylacetate

HRID 495279Notes

Reaction equation

HRID 495279 reaction equation
Br[C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=1[CH2:16][C:17]([O:19][CH3:20])=[O:18].[CH:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[CH:21]([C:23]1[CH:28]=[C:27]([C:2]2[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=2[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:26]=[CH:25][CH:24]=1)=[O:22]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27343563-Formylphenylboronic acidHCID 68420121Methyl 2-bromo-3,5-bis(methoxymethoxy)phenylacetate

Product 1

HCID 86613495Methyl 2-(3-formylphenyl)-3,5-bis(methoxymethoxy)phenylacetateYield 75%

Reagents, catalysts & solvents 3

HCID 178424406HCID 178424406, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Methyl 2-bromo-3,5-bis(methoxymethoxy)phenylacetate (630 mg, 1.8 mmol)-obtained in the step 2 in Example 1 was dissolved in a mixed solvent of 1,2-dimethoxyethane (10 mL) and water (2 mL), and in an argon atmosphere, 3-formylphenylboronic acid (400 mg, 2.7 mmol), bis(tri-o-tolylphosphine)palladium(II) dichloride (140 mg, 0.17 mmol) and cesium carbonate (1.1 g, 7.2 mmol) were added thereto, and stirred under heat for 10 hours. The reaction mixture was cooled to room temperature, then filtered, and the filtrate was concentrated under reduced pressure. Water was added to the resulting residue, and extracted twice with ethyl acetate. The organic layer was dried over anhydrous sodium 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 methyl 2-(3-formylphenyl)-3,5-bis(methoxymethoxy)phenylacetate (500 mg, 75%).

Workup

  1. temperatureunder heat for 10 hours
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater was added to the resulting residue
  5. extractionextracted twice with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated away under reduced pressure
  8. customThe resulting residue was purified through silica gel column chromatography (ethyl acetate/n-hexane=1/4 to 1/2)

Sources & evidence

ORD record
ord-8cf20890d64e481aa77ccce4a57d86a9
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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