Toluene → 1-methoxy-2-oxabicyclo[3.3.0]octane

HRID 2113244Notes

Reaction equation

HRID 2113244 reaction equation
[C:1]1(C)C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C([O:28][CH2:29][CH2:30][CH:31]1[CH2:35][CH2:34][CH2:33][C:32]1=[O:36])(=O)C>CO>[CH3:1][O:36][C:32]12[CH2:33][CH2:34][CH2:35][CH:31]1[CH2:30][CH2:29][O:28]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11116481HCID 11116481, compound

Product 1

HCID 103517951-methoxy-2-oxabicyclo[3.3.0]octaneYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction vessel was charged with 21 parts of anhydrous toluene, 0.6 parts of methanol, 0.2 part of pyridinium paratoluene sulfonate (PPTS), 2.0 parts of 2-(2-acetoxyethyl)cyclopentanone (8) obtained in Preparation Example 1 at room temperature. The mixture was refluxed for seven hours with stirring. After the reaction, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=19:1) to obtain 1.6 parts of 1-methoxy-2-oxabicyclo[3.3.0]octane (9) (yield: 95%).

Workup

  1. customobtained in Preparation Example 1 at room temperature
  2. temperatureThe mixture was refluxed for seven hours
  3. customAfter the reaction
  4. filtrationthe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=19:1)

Sources & evidence

ORD record
ord-dee7a8fcf4544cc6b84b1b90e4fb64f7
Source dataset
uspto-grants-2009_04
Patent number
US07524978B2

Reaction notes

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