Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86673390, compound

HRID 1023360Notes

Reaction equation

HRID 1023360 reaction equation
[Si]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19](/[C:23](/[CH3:34])=[CH:24]/[C:25]([O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])=[O:26])=[CH:18][C:17]=2[Cl:35])=[N:13][CH:14]=1)(C(C)(C)C)(C)C.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CCO>[Cl:35][C:17]1[CH:18]=[C:19](/[C:23](/[CH3:34])=[CH:24]/[C:25]([O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])=[O:26])[CH:20]=[C:21]([CH3:22])[C:16]=1[O:15][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86673391HCID 86673391, compound

Product 1

HCID 86673390HCID 86673390, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(trimethylsilyl)ethyl (E)-3-{4-[(5-{[tert-butyl(dimethyl)silyl]-oxy}pyridin-2-yl)oxy]-3-chloro-5-methylphenyl}but-2-enoate (0.630 g) in EtOH (12 mL) was added PPTS (0.296 g) at room temperature, then the reaction mixture was stirred for 4 days. The reaction mixture was warmed to 60° C., and stirred over night. The reaction mixture was concentrated under reduced pressure. The residue was diluted with pH 7 phosphate buffer, 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=8/1 to 2/1) to afford 2-(trimethylsilyl)ethyl (E)-3-{3-chloro-4-[(5-hydroxypyridin-2-yl)oxy]-5-methylphenyl}but-2-enoate as a colorless oil (0.490 g).

Workup

  1. stirringstirred over night
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with pH 7 phosphate buffer
  4. extractionextracted with AcOEt
  5. washThe organic layer was washed with water and saturated aqueous NaCl
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=8/1 to 2/1)

Sources & evidence

ORD record
ord-59eec9080df24d058fdc6ffd201bb574
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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