Hydrochloric Acid → HCID 23143912, compound

HRID 1985821Notes

Reaction equation

HRID 1985821 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](=[O:21])([O-])[O-].[Na+].[Na+].[OH2:24].Cl.C[N:27]([CH3:30])C=O>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:10]=[C:11]([C:2]2[CH:7]=[CH:6][C:5]([C:30]#[N:27])=[CH:4][C:3]=2[O:24][CH2:14][CH2:9][CH2:10][CH2:18][OH:21])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 27343133-Benzyloxy-phenylboronic acid

Product 1

HCID 23143912HCID 23143912, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

4-Hydroxy-3-(4-hydroxybutoxy)benzonitrile (1.0 g) and pyridine (1.9 mL) were dissolved in dichloromethane (15 mL), and to the mixture was added dropwise trifluoromethanesulfonic anhydride (1.7 mL) under ice-cooling. The mixture was stirred at room temperature for 30 minutes, and to the reaction mixture was added 1 mol/L hydrochloric acid (50 mL). The resulting mixture was extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine successively and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give trifluoromethanesulfonic acid ester. The obtained trifluoromethanesulfonic acid ester, 3-benzyloxyphenylboronic acid (1.3 g), sodium carbonate (1.0 g), tetrakis(triphenylphosphine)palladium (0.3 g) and water (2 mL) were suspended in N,N-dimethylformamide (15 mL), and the mixture was stirred at 80° C. for 12 hours. To the reaction mixture was added dropwise 1 mol/L hydrochloric acid (30 mL), and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate/hexane=1/5) to give the title compound (0.8 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-11fad7b06922448695dd1be59bd841b1
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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