反応 #57440

反応方程式

di-tert-butyl azodicarboxylate

N-hydroxylphthalimide

triphenylphosphine

tetrahydro-4H-pyran-4-ol

→

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

溶媒

THF

反応条件

後処理

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

実験手順

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).

出典