تفاعل #52655

معادلة التفاعل

diethylazodicarboxylate

Triphenylphosphine

3,5-diisopropyl-4-hydroxybenzaldehyde

2-hydroxyethylmorpholine

→

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

المردود 14.4%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   تركيزThe reaction was concentrated under reduced pressure
2. 2
   أخرىpartitioned between 2N hydrochloric acid (200 ml) and ethyl acetate (150 ml)
3. 3
   استخلاصThe aqueous layer was extracted with ethyl acetate (2×150ml)
4. 4
   استخلاصextracted with ethyl acetate (3×150 ml)
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   تركيزconcentrated

الإجراء التجريبي

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.

المصدر