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

HRID 874519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 874519
[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]

Komponenten

6

Edukt 2

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

Produkt 1

HCID 2895872-(Oxan-2-yloxy)isoindole-1,3-dioneAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-13cb4623d1bd43ea94c508923fd50c3a
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980909B2

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