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

HRID 495177Notes

Reaction equation

HRID 495177 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6](Br)=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1.[C:21]1(OB(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd][P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 78412Phenyl dihydrogen orthoborateHCID 68420121Methyl 2-bromo-3,5-bis(methoxymethoxy)phenylacetate

Product 1

HCID 23116311Methyl 3,5-bis(methoxymethoxy)-2-phenylphenylacetate

Reagents, catalysts & solvents 2

HCID 178424408HCID 178424408, compoundCatalystHCID 962WaterSolvent

Procedure

Methyl 3,5-bis(methoxymethoxy)-2-bromophenylacetate (15.0 g, 43.0 mmol) obtained in Example 3, Step 1 was dissolved in a mixed solvent of 1,2-dimethoxymethane (0.15 L) and water (6.0 mL). To the solution were added phenylboric acid (7.3 g, 60 mmol), bis(tri-o-tolylphosphine)palladium (II) dichloride (0.68 g, 0.86 mmol) and cesium carbonate (42 g, 0.13 mol) in an atmosphere of argon, followed by stirring for 16.5 hours under heating and reflux. After cooling to room temperature, the reaction mixture was filtered under reduced pressure, and the filtrate was concentrated under reduced pressure. To the resulting residue was added water (0.50 L), followed by extraction with ethyl acetate (0.40 L×2). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/3) to obtain a quantitative yield of methyl 3,5-bis(methoxymethoxy)-2-phenylphenylacetate.

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. filtrationthe reaction mixture was filtered under reduced pressure
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the resulting residue was added water (0.50 L)
  6. extractionfollowed by extraction with ethyl acetate (0.40 L×2)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/3)

Sources & evidence

ORD record
ord-53bd78ad67e3420da1d87b06773a6b3c
Source dataset
uspto-grants-2009_05
Patent number
US07538224B2

Reaction notes

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