반응 #9631

반응 방정식

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

수율 55.0%

용매

dichloromethane

반응 조건

후처리

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

실험 절차

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).

출처