Reaktion #57440

Reaktionsgleichung

di-tert-butyl azodicarboxylate

N-hydroxylphthalimide

triphenylphosphine

tetrahydro-4H-pyran-4-ol

→

2-(tetrahydro-2H-pyran-4-yloxy)-1H-isoindole-1,3(2H)-dione

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewere transferred to a flask
2. 2
   SonstigeThe solvent was removed under vacuum
3. 3
   workup.STIRRINGThe reaction was stirred for 30 minutes
4. 4
   Sonstigethe TFA was removed under vacuum
5. 5
   workup.DISSOLUTIONThe crude residue was then dissolved in ethyl acetate
6. 6
   Waschenwashed with a saturated aqueous solution of sodium bicarbonate, 5% aqueous solution of potassium carbonate, brine
7. 7
   Trocknendried over magnesium sulfate
8. 8
   SonstigeThe solvent was removed under vacuum
9. 9
   Sonstigethe residual triphenylphosphine oxide was crystallized
10. 10
    Filtrationfiltered
11. 11
    SonstigeThe solvent was again removed
12. 12
    Sonstigethe crude solid was purified by silica gel chromatography (2:1 hexanes/ethyl acetate) and recrystallization

Vorschrift

A light suspension containing N-hydroxylphthalimide (18.4 mmol, 3.0 g), triphenylphosphine (18.4 mmol, 4.82 g), tetrahydro-4H-pyran-4-ol (18.4 mmol, 1.75 mL) and anhydrous THF (50 mL), were transferred to a flask containing di-tert-butyl azodicarboxylate (20.2 mmol, 4.66 g) under nitrogen. Over 2 hours the reaction stirred at room temperature and changed from a dark orange to yellow in appearance. The solvent was removed under vacuum and replaced with trifluoroacetic acetic acid (10 mL). The reaction was stirred for 30 minutes and the TFA was removed under vacuum. The crude residue was then dissolved in ethyl acetate, washed with a saturated aqueous solution of sodium bicarbonate, 5% aqueous solution of potassium carbonate, brine and dried over magnesium sulfate. The solvent was removed under vacuum and the residual triphenylphosphine oxide was crystallized and filtered using hexanes and ether. The solvent was again removed and the crude solid was purified by silica gel chromatography (2:1 hexanes/ethyl acetate) and recrystallization using methylene chloride and hexanes providing 1.69 g (37%) of a white crystal. Rf=0.3 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.84-7.82 (2H,m), 7.75-7.73(2H,m), 4.46-4.40 (1H,m), 4.08-4.02 (2H,m), 3.50-3.44 (2H,m), 2.04-1.98 (2H,m), 1.92-1.84 (2H,m).

Quelle