p-Toluenesulfonic acid → HCID 10538042, compound

HRID 862861Notes

Reaction equation

HRID 862861 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]1([CH3:16])[CH:11]=[CH:10][C:9]([S:12](O)(=O)=O)=[CH:8]C=1>CO>[CH2:10]([C:9]1[S:12][C:4]([CH2:3][CH2:2][OH:1])=[CH:5][CH:8]=1)[CH2:11][CH2:6][CH2:16][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 8028Tetrahydrofuran

Product 1

HCID 10538042HCID 10538042, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tetrahydrofuran (20 ml) and p-toluenesulfonic acid (0.3 g) were added to a solution (80 ml) of the above-mentioned compound (6.5 g) in methanol and the mixture was stirred at room temperature for 1 hour. The solvent was distilled away and ethyl acetate was added to the resulting mixture. The mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled away and the residue obtained was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1) to give 4 g of the subject compound as an oil.

Workup

  1. distillationThe solvent was distilled away
  2. additionethyl acetate was added to the resulting mixture
  3. washThe mixture was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled away
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-e23f19b587ea47cbaf00ac08e15d1a4d
Source dataset
uspto-grants-1998_02
Patent number
US05719176

Reaction notes

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