تفاعل #412073

معادلة التفاعل

di-tert-butyl 1,3-acetonedicarboxylate

3,5-heptanedione

sodium methoxide

→

oil

المردود 97.5%

Di-tert-butyl 4,6-diethyl-2-hydroxy-1,3-benzenedicarboxylate

المردود 97.5%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   أخرىMethanol was removed via rotary evaporation
2. 2
   أخرىthe resulting orange sludge was partitioned between diethyl ether (100 mL) and 10% aqueous hydrochloric acid (100 mL)
3. 3
   استخلاصThe separated aqueous layer was extracted with diethyl ether (50 mL×2)
4. 4
   غسيلThe combined organic portions were washed with saturated aqueous sodium chloride (20 mL)
5. 5
   تجفيفdried over sodium sulfate
6. 6
   ترشيحfiltered through a pad of silica (20 mm×40 mm)
7. 7
   تركيزconcentrated in vacuo

الإجراء التجريبي

A mixture of di-tert-butyl 1,3-acetonedicarboxylate (10 g, 38.7 mmol), 3,5-heptanedione (6.5 g, 50.3 mmol) and sodium methoxide (2.7 g, 50.3 mmol) in methanol (100 mL) was stirred at room temperature overnight. Methanol was removed via rotary evaporation and the resulting orange sludge was partitioned between diethyl ether (100 mL) and 10% aqueous hydrochloric acid (100 mL). The separated aqueous layer was extracted with diethyl ether (50 mL×2). The combined organic portions were washed with saturated aqueous sodium chloride (20 mL), dried over sodium sulfate, filtered through a pad of silica (20 mm×40 mm) and concentrated in vacuo to yield a yellow oil (13.23 g, 97%): 1H NMR (300 MHz, CDCl3): δ 1.20 (t, 6H), 1.60 (s, 18H) 2.74 (q, 4H), 6.55 (s, 1H), 11.73 (s, 1H).

المصدر