Reaktion #332116

Reaktionsgleichung

isobutyryl chloride

lithiumdiisopropylamine

ethyl 2-(4-hexylphenyl)acetate

→

desired product

Ausbeute 70.5%

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

Ausbeute 70.5%

Lösungsmittel

hexane tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe solution was warmed to 0° C.
2. 2
   TemperaturThe reactuion solution was cooled to −60° C. again
3. 3
   SonstigeThe reaction was quenched with saturated aqueous sodium hydrogen carbonate (150 ml)
4. 4
   Extraktionthe reaction solution was extracted with ethyl acetate
5. 5
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenthe filtrate was concentrated under reduced pressure
8. 8
   SonstigeThe resulting residue was purified by silica gel column chromatography

Vorschrift

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.

Quelle