p-Toluenesulfonic acid → HCID 19886006, compound

HRID 654915Notes

Reaction equation

HRID 654915 reaction equation
[C:1]([O:4][CH:5]([C:15]1[CH:19]([OH:20])[O:18][C:17](=[O:21])[CH:16]=1)[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2].[C:22]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([O:4][CH:5]([C:15]1[CH:19]([O:20][CH3:22])[O:18][C:17](=[O:21])[CH:16]=1)[CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15723398HCID 15723398, compound

Product 1

HCID 19886006HCID 19886006, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(1-acetoxy-4-phenylbutyl)-5-hydroxy-2(5H)-furanone (0.020 g., 0.069 mmol) and p-toluene sulfonic acid (approx. 3 mg.) in 2.5 ml methanol was stirred for 72 hours at room temperature. The reaction mixture was concentrated and partitioned between ethyl ether and water. The organic portion was washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give an oil (0.027 g.) This material was purified by flash chromatography (30% ethyl acetate/hexane) to give a diasteriomeric mixture of the two methoxybutenolides. The mixture was subsequently separated by semi-preparative HPLC on a Whatman Partisil M-9 silica column, with an elution rate of 4 ml/min with 20% ethyl acetate/hexane. One diasteriomer (A) was eluted at 11 minutes, followed by the other (B) at 12 minutes. Concentration gave the purified compounds.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl ether and water
  3. washThe organic portion was washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil (0.027 g.) This material
  8. customwas purified by flash chromatography (30% ethyl acetate/hexane)
  9. customto give
  10. customThe mixture was subsequently separated by semi-preparative HPLC on a Whatman Partisil
  11. washOne diasteriomer (A) was eluted at 11 minutes
  12. concentrationConcentration
  13. customgave the purified compounds

Sources & evidence

ORD record
ord-4f13f69b980d4e5e8f7f807dd973dcfe
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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