Water → HCID 23062463, compound

HRID 2109372Notes

Reaction equation

HRID 2109372 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1.O.[C:30]([O:33][CH2:34][CH3:35])(=[O:32])C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:25]1[CH:24]=[CH:28][O:27][C:26]=1[C:30]([O:33][CH2:34][CH3:35])=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 2773253(2-(Benzyloxy)phenyl)boronic acid

Product 1

HCID 23062463HCID 23062463, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of the compound of Reference Example 1 (2.20 g), 2-benzyloxyphenylboronic acid (3.40 g), tetrakis(triphenylphosphine)palladium (1.20 g) and cesium carbonate (4.90 g) in a mixed solvent of THF (30 ml) and water (15 ml) were heated at reflux overnight under an argon atmosphere. After cooling, the reaction solution was diluted with ethyl acetate, and the organic layer was dried over MgSO4. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/20), thereby giving 3.40 g of ethyl 3-(2-benzyloxyphenyl)-2-furancarboxylate.

Workup

  1. temperaturewere heated
  2. temperatureat reflux overnight under an argon atmosphere
  3. temperatureAfter cooling
  4. dry with materialthe organic layer was dried over MgSO4
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/20)

Sources & evidence

ORD record
ord-65429bc6a7cf4f03b77b3416e738a683
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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