Water → HCID 23062461, compound

HRID 2109371Notes

Reaction equation

HRID 2109371 reaction equation
[C:1](=[O:4])([O-])[O-:2].[Cs+].[Cs+].[CH2:7]1[CH2:11][O:10][CH2:9][CH2:8]1.[OH2:12].[C:13]1(C)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>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>[OH:12][C:13]1[CH:14]=[C:15]([C:8]2[CH:7]=[CH:11][O:10][C:9]=2[C:1]([OH:2])=[O:4])[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 8028TetrahydrofuranHCID 10796Cesium carbonate

Product 1

HCID 23062461HCID 23062461, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of the compound of Reference Example 1 (1.5 g), 3-hydroxyphenylboronic acid pinacol cyclic ester (2.4 g), tetrakis(triphenylphosphine)palladium (0.8 g) and cesium carbonate (3.5 g) were heated at reflux in a mixed solvent of THF (20 ml) and water (10 ml) for 16 hours under an argon atmosphere. After cooling, toluene was added to the reaction solution, and extracted with a 5% aqueous sodium hydroxide solution. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was successively washed with water and saturated brine, and the solvent was evaporated under reduced pressure, thereby giving 1.4 g of the desired compound (1.4 g).

Workup

  1. temperaturewere heated
  2. temperatureAfter cooling
  3. extractionextracted with a 5% aqueous sodium hydroxide solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was successively washed with water and saturated brine
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f7516124286342dc99b6c68a289cc1c8
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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