반응 #318315

반응 방정식

1-[4,5-(methylenedioxy)-2-(phenylmethoxy)phenyl]ethanone

sodium hydride

dimethylcarbonate

→

methyl 4,5-(methylenedioxy)-β-oxo-2-(phenylmethoxy)benzenepropanoate

수율 91.3%

반응 조건

후처리

1. 1
   온도was heated to 70°-75° C. for 20 minutes
2. 2
   기타After evaporating the excess dimethylcarbonate under reduced pressure
3. 3
   추출extracted with ether
4. 4
   세척The ether solution was washed with water
5. 5
   건조dried (Na2SO4)
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure
8. 8
   여과The crude product was filtered through silica gel

실험 절차

A mixture of 1-[4,5-(methylenedioxy)-2-(phenylmethoxy)phenyl]ethanone (5.4 g, 0.02 mol), sodium hydride (1.6 g of 60% sodium hydride, 0.04 mol) and dimethylcarbonate (18 g, 0.2 mol) was heated to 70°-75° C. for 20 minutes. After evaporating the excess dimethylcarbonate under reduced pressure, the residue was acidified with 10% HCl solution and extracted with ether. The ether solution was washed with water, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was filtered through silica gel using chloroform as eluent to afford 5.99 g (91.3%) of methyl 4,5-(methylenedioxy)-β-oxo-2-(phenylmethoxy)benzenepropanoate mp (EtOH) 86°-86.5° C.; IR (KBr) 1750 (ester), 1652 (carbonyl) cm-1 ; NMR (CDCl3, 90 MHz) δ, 3.61 (S, 3H, CO2CH3), 3.92 (S, 2H, CH2CO2CH3), 5.11 (S, 2H, CH2Ph), 5.98 (S, 2H, OCH2O), 6.54 (S, 1H, ArH), 7.39 (S, 5H, CH2Ph), 7.41 (S, 1H, ArH). Anal. calcd. for C18H16O6 : C, 65.85; H, 4.91. Found: C, 65.92; H, 5.11.

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