Cyclohexanol → N-cyclohexyloxyphthalimide

HRID 29200

Reaktionsgleichung

Reaktionsgleichung von HRID 29200
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCCC1>[CH:1]1([O:7][N:9]2[C:13](=[O:14])[C:12]3[C:11](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]2=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 7966CyclohexanolHCID 10665N-HydroxyphthalimideHCID 97268Di-tert-butyl azodicarboxylate2×

Produkt 1

HCID 10467039N-cyclohexyloxyphthalimideAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A solution of triphenylphosine (15.53 g, 59.2 mmol), cyclohexanol (6.25 mL, 59.2 mmol), and N-hydroxypthalimide (9.66 g, 59.2 mmol) in anhydrous tetrahydrofuran (500 mL) under Argon was treated dropwise over approximately 20 minutes with a solution of di-tert-butyl azodicarboxylate (15.00 g, 65.14 mmol) in tetrahydrofuran (100 mL) with a water bath to control the exotherm. After the reddish color had dissipated, a mixture of di-tert-butyl azodicarboxylate (3.00 g, 13.0 mmol) and triphenylphosine (3.11 g, 11.8 mmol) in anhydrous tetrahydrofuran (50 mL) was added to the reaction mixture and allowed to stir overnight at ambient temperature. After evaporation in vacuo, the residue was treated with trifluoroacetic acid (100 mL) and stirred for 20 minutes. The reaction was evaporated in vacuo and the residue was partitioned between water and dichloromethane. The layers were separated and the aqueous phase was extracted with dichloromethane. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to a residue. The crude material was purified twice by flash silica gel chromatography eluting with hexane:ethyl acetate (4:1 and 9:1). Pure fractions were concentrated in vacuo to a solid and dried under high vacuum to provide 2-(cyclohexyloxy)-1H-isoindole-1,3(2H)-dione as a solid (10.90 g, 75%).

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. customAfter evaporation in vacuo
  3. additionthe residue was treated with trifluoroacetic acid (100 mL)
  4. stirringstirred for 20 minutes
  5. customThe reaction was evaporated in vacuo
  6. customthe residue was partitioned between water and dichloromethane
  7. customThe layers were separated
  8. extractionthe aqueous phase was extracted with dichloromethane
  9. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo to a residue
  12. customThe crude material was purified twice by flash silica gel chromatography
  13. washeluting with hexane:ethyl acetate (4:1 and 9:1)
  14. concentrationPure fractions were concentrated in vacuo to a solid
  15. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ddaa3817a9204ead8417483ef2c25e76
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419967B2

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