p-Toluenesulfonic acid → HCID 86673389, compound

HRID 1023358Notes

Reaction equation

HRID 1023358 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:23]=[C:24](\[CH3:30])/[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:5]=[C:6]([CH3:22])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C2CCCCO2)=[CH:11][N:10]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCO>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:23]=[C:24](\[CH3:30])/[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:5]=[C:6]([CH3:22])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 67328630HCID 67328630, compound

Product 1

HCID 86673389HCID 86673389, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl (E)-3-(3-chloro-5-methyl-4-{[5-(tetrahydro-2H-pyran-2-yloxy)pyridin-2-yl]oxy}phenyl)-2-methylprop-2-enoate (2.58 g) in EtOH (40 mL) was added p-toluenesulfonic acid (1.14 g) at room temperature, then the reaction mixture was stirred for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was diluted with H2O, and extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=10/1 to 2/1) to afford ethyl (E)-3-{3-chloro-4-[(5-hydroxypyridin-2-yl)oxy]-5-methylphenyl}-2-methylprop-2-enoate as a colorless amorphous (1.98 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with H2O
  3. extractionextracted with AcOEt
  4. washThe organic layer was washed with water and saturated aqueous NaCl
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=10/1 to 2/1)

Sources & evidence

ORD record
ord-12aa76cb331c472184b442e2b4bdfc88
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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