反応 #49633

反応方程式

ethyl acetoacetate

sodium

2-bromomethylnaphthalene

→

2-(2-ethoxycarbonyl-3-oxobutyl)naphthalene

収率 114.1%

溶媒

ethanol

ethanol

ethanol

反応条件

後処理

1. 1
   その他In a four-necked flask equipped with a thermometer
2. 2
   その他to form a solution
3. 3
   workup.ADDITIONAfter completion of the addition
4. 4
   その他was brought up to 65° C.
5. 5
   workup.DISTILLATIONwas distilled off under reduced pressure
6. 6
   その他the residue obtained
7. 7
   抽出was extracted by addition of 1500 ml of toluene
8. 8
   その他the organic layer was separated
9. 9
   洗浄The organic layer was washed with 10% hydrochloric acid, water, 5% aqueous sodium bicarbonate solution and water in said order
10. 10
    濃縮concentrated under reduced pressure

実験手順

In a four-necked flask equipped with a thermometer, dropping funnel and stirrer were placed 179 g (1.375 moles) of ethyl acetoacetate and 500 ml of ethanol, and then 31.5 g (1.375 moles) of sodium was added in portions thereto to form a solution. Then, a solution of 276.4 g (1.25 moles) of 2-bromomethylnaphthalene in 1000 ml of ethanol was added dropwise to the above solution at room temperature over a period of 2 hours. After completion of the addition, the resulting mixture was brought up to 65° C. and stirred at the same temperature for 6 hours. After completion of the reaction ethanol was distilled off under reduced pressure, the residue obtained was extracted by addition of 1500 ml of toluene, and the organic layer was separated. The organic layer was washed with 10% hydrochloric acid, water, 5% aqueous sodium bicarbonate solution and water in said order and then concentrated under reduced pressure to obtain 385.4 g of 2-(2-ethoxycarbonyl-3-oxobutyl)naphthalene as a crude product.

出典