تفاعل #332116

معادلة التفاعل

isobutyryl chloride

lithiumdiisopropylamine

ethyl 2-(4-hexylphenyl)acetate

→

desired product

المردود 70.5%

ethyl 2-(4-hexylphenyl)-4-methyl-3-oxopentanoate

المردود 70.5%

المذيبات

hexane tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe solution was warmed to 0° C.
2. 2
   درجة الحرارةThe reactuion solution was cooled to −60° C. again
3. 3
   أخرىThe reaction was quenched with saturated aqueous sodium hydrogen carbonate (150 ml)
4. 4
   استخلاصthe reaction solution was extracted with ethyl acetate
5. 5
   تجفيفThe organic layer was dried over anhydrous magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزthe filtrate was concentrated under reduced pressure
8. 8
   أخرىThe resulting residue was purified by silica gel column chromatography

الإجراء التجريبي

6.0 g (24 mmol) of ethyl 2-(4-hexylphenyl)acetate was dissolved in 130 mL of dry tetrahydrofuran under a nitrogen atmosphere and cooled to −60° C. After addition of 31.8 mL (36.2 mmol) of 1.14 M solution of lithiumdiisopropylamine in hexane/tetrahydrofuran, the solution was warmed to 0° C. and stirred for 1 hours. The reactuion solution was cooled to −60° C. again and stirred with 3.6 g (34 mmol) of isobutyryl chloride at −60° C. to room temperature for 15 hours. The reaction was quenched with saturated aqueous sodium hydrogen carbonate (150 ml), and the reaction solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate:hexane (0:100 to 1:9) as the eluent to give 5.39 g of the desired product as a pale yellw oil.

المصدر