反応 #59128

反応方程式

methyl 4-(2-chloro-2-oxoethyl)tetrahydro-2H-pyran-4-carboxylate

bromobenzene

aluminum chloride

→

methyl 4-[2-(4-bromo-phenyl)-2-oxoethyl]tetrahydro-2H-pyran-4-carboxylate

収率 55.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他The ice-water bath was removed
2. 2
   温度The mixture was then cooled at 0° C.
3. 3
   その他quenched by the addition of 1 N HCl solution and water
4. 4
   抽出The mixture was extracted with dichloromethane
5. 5
   乾燥the combined organic phases were dried over sodium sulfate
6. 6
   その他The crude material was then purified by flash chromatography (Biotage Flash 40 M, 2:1 hexane/ethyl acetate

実験手順

Step 5 To a solution of methyl 4-(2-chloro-2-oxoethyl)tetrahydro-2H-pyran-4-carboxylate (1.06 g, 4.8 mmol) and bromobenzene (1.13 g, 7.21 mmol) in dichloromethane (20 mL) at 0° C. was added aluminum chloride (1.92 g, 14.4 mmol). The ice-water bath was removed and the reaction mixture was stirred at rt for 16 h. The mixture was then cooled at 0° C. and quenched by the addition of 1 N HCl solution and water. The mixture was extracted with dichloromethane, and the combined organic phases were dried over sodium sulfate. The crude material was then purified by flash chromatography (Biotage Flash 40 M, 2:1 hexane/ethyl acetate, to afford methyl 4-[2-(4-bromo-phenyl)-2-oxoethyl]tetrahydro-2H-pyran-4-carboxylate (900 mg, 55%). LC-MS ret. time 2.76 min; m/z 342.9 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.58-1.69 (m, 2H), 2.12-2.18 (m, 2H), 3.28 (s, 2H), 3.64 (s, 3H), 3.69-3.77 (m, 4H), 7.59 (d, 2H), 7.77 (d, 2H).

出典