p-Toluenesulfonic acid monohydrate → HCID 21086214, compound

HRID 14247Notes

Reaction equation

HRID 14247 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([OH:17])([C:13]([O:15][CH3:16])=[O:14])[CH2:6][C:7]=1[C:8](=[O:12])[CH2:9][CH2:10][CH3:11].O.C1(C)C=CC(S(O)(=O)=[O:26])=CC=1>O.O1CCCC1>[C:8]([CH:7]1[CH2:6][C:5]([OH:17])([C:13]([O:15][CH3:16])=[O:14])[CH:4]=[CH:3][C:2]1=[O:26])(=[O:12])[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21086195Methyl 4-amino-5-butyryl-1-hydroxycyclohexa-2,4-diene-1-carboxylate

Product 1

HCID 21086214HCID 21086214, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirred solution of methyl 4-amino-5-butyryl-1-hydroxycyclohexa-2,4-diene-1-carboxylate (1.25 g, 5.2 mmol) in a 1:1 mixture of water/tetrahydrofuran (10 mL) was added p-toluenesulfonic acid monohydrate (1.1 g, 5.8 mmol). The reaction mixture was stirred for 18 h and then partitioned between dichloromethane and water. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to afford methyl 5-butyryl-1-hydroxy-4-oxocyclohex-2-ene-1-carboxylate which was used without further purification or characterization.

Workup

  1. custompartitioned between dichloromethane and water
  2. dry with materialThe organic layer was dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a9243cff28314fbdaf984d393ac96b0e
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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