p-Toluenesulfonic acid monohydrate → HCID 71271002, compound

HRID 1752509Notes

Reaction equation

HRID 1752509 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:11])=[CH:9][C:8]([C:12]([O:14]CC)=[CH2:13])=[CH:7][N:6]=1)=[O:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1.CC(OC)(C)C.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:11])=[CH:9][C:8]([C:12](=[O:14])[CH3:13])=[CH:7][N:6]=1)=[O:4]

Participants

6

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86689176HCID 86689176, compound

Product 1

HCID 71271002HCID 71271002, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-chloro-5-(1-ethoxy-vinyl)-pyridine-2-carboxylic acid methyl ester (359 mg, 1.485 mmol) in THF (3.6 ml) was added para-toluenesulfonic acid monohydrate (565 mg, 2.97 mmol) and the mixture was stirred for 1 h. The reaction mixture was diluted with TBME and sat. aq. NaHCO3, the layers were separated and the aq. Phase was extracted with TBME. The combined organic layers were washed with sat. aq. NaHCO3 and sat. aq. NaCl, dried with MgSO4, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EtOAc 9:1 to 6/1) to provide the title compound as yellow solid.

Workup

  1. customthe layers were separated
  2. extractionthe aq. Phase was extracted with TBME
  3. washThe combined organic layers were washed with sat. aq. NaHCO3 and sat. aq. NaCl
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (cyclohexane/EtOAc 9:1 to 6/1)

Sources & evidence

ORD record
ord-eee9d074c9da4055953ac5328b6c0c58
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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