반응 #52655

반응 방정식

diethylazodicarboxylate

Triphenylphosphine

3,5-diisopropyl-4-hydroxybenzaldehyde

2-hydroxyethylmorpholine

→

3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde

수율 14.4%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   농축The reaction was concentrated under reduced pressure
2. 2
   기타partitioned between 2N hydrochloric acid (200 ml) and ethyl acetate (150 ml)
3. 3
   추출The aqueous layer was extracted with ethyl acetate (2×150ml)
4. 4
   추출extracted with ethyl acetate (3×150 ml)
5. 5
   건조dried over magnesium sulfate
6. 6
   농축concentrated

실험 절차

Triphenylphosphine (5.14 g, 19.58 mmol) was added to a solution of 3,5-diisopropyl-4-hydroxybenzaldehyde (4 g, 19.58 mmol) in tetrahydrofuran (40 ml) followed by addition of 2-hydroxyethylmorpholine (2.57 g, 19.58 mmol) and then the dropwise addition of diethylazodicarboxylate (3.41 g, 19.58 mmol). The mixture was stirred at room temperature for 12 hours. The reaction was concentrated under reduced pressure and partitioned between 2N hydrochloric acid (200 ml) and ethyl acetate (150 ml). The aqueous layer was extracted with ethyl acetate (2×150ml), basified to pH 9 with solid sodium bicarbonate and extracted with ethyl acetate (3×150 ml). The organic layers were combined, dried over magnesium sulfate and concentrated to afford 900 mg (14%) of 3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde as a yellowish oil.

출처