3,4-dihydro-2H-pyran → 2-(oxan-2-yloxy)isoindole-1,3-dione

HRID 874519Notes

Reaction equation

HRID 874519 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1>C(Cl)Cl.O1CCOCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7]

Participants

6

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 10665N-Hydroxyphthalimide

Product 1

HCID 2895872-(oxan-2-yloxy)isoindole-1,3-dioneYield 88.3%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

to a vigorously stirred solution of N-hydroxyphthalimide (10.0 g, 61.4 mmol) in CH2Cl2 (70 mL) and dioxane (80 mL) was added dihydropyran (6.16 mL, 67.6 mmol) and p-toluenesulfonic acid (200 mg). The resulting solution was stirred overnight at room temperature. The reaction was quenched by slow addition of saturated NaHCO3 (100 mL). After separation, the organic layer was washed with brine and dried over Na2SO4. Solvent removal under vacuum yielded 13.4 g (88%) of 2-(tetrahydro-2H-pyran-2-yloxy)isoindoline-1,3-dione as a white solid.

Workup

  1. customThe reaction was quenched by slow addition of saturated NaHCO3 (100 mL)
  2. customAfter separation
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customSolvent removal under vacuum

Sources & evidence

ORD record
ord-13cb4623d1bd43ea94c508923fd50c3a
Source dataset
uspto-grants-2015_03
Patent number
US08980909B2

Reaction notes

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