p-Toluenesulfonic acid monohydrate → HCID 22284233, compound

HRID 1061665Notes

Reaction equation

HRID 1061665 reaction equation
[CH:1]([O-])([O-])[O:2]C.O.[C:7]1(C)C=CC(S(O)(=O)=O)=CC=1.[O:18]=[C:19]([CH2:27][CH3:28])[CH2:20][S:21][CH2:22][C:23]([O:25][CH3:26])=[O:24].C[O-].[Na+]>CO>[CH3:7][O:18][C:19]([O:2][CH3:1])([CH2:27][CH3:28])[CH2:20][S:21][CH2:22][C:23]([O:25][CH3:26])=[O:24]

Participants

6

Reactant 4

HCID 521998p-Toluenesulfonic acid monohydrateHCID 10942334Sodium MethoxideHCID 12353742Methyl [(2-oxobutyl)sulfanyl]acetateHCID 53629101Methylorthoformate

Product 1

HCID 22284233HCID 22284233, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Methyl orthoformate (10.8 ml) and p-toluenesulfonic acid monohydrate. (catalytic amount) are added to a solution of methyl 2-(2-oxobutylthio)acetate (5.80 g, Reference compound No. 36-1) in methanol (60 ml), and the mixture is refluxed for two hours. The reaction mixture is cooled to 0° C., sodium methoxide (1.98 g) is added to the mixture, and the whole is stirred for 20 minutes. The reaction mixture is concentrated under reduced pressure, ethyl acetate is added to the resulting residue, and the whole is washed with saturated brine. The organic layer is dried over anhydrous magnesium sulfate, and the solvent is distilled away under reduced pressure to give the titled reference compound (6.85 g).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure, ethyl acetate
  2. additionis added to the resulting residue
  3. washthe whole is washed with saturated brine
  4. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled away under reduced pressure

Sources & evidence

ORD record
ord-b8d240fab5b1451b9944a155dd46a5c8
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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