Ethanol → Ethyl (2-chlorobenzoyl)acetate

HRID 878487

반응식

HRID 878487 반응식
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[O:20])[CH3:19].C(O)C>C1COCC1>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[O:20])[CH2:19][C:3]([O:7][CH2:8][CH3:9])=[O:10]

참가 물질

6

반응물 4

HCID 702Ethanol2회HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 72864Ethanone, 1-(2-chlorophenyl)-

생성물 1

HCID 292405Ethyl (2-chlorobenzoyl)acetate수율 34%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

Sodium hydride (1.45 g, 36 mmol) and diethyl carbonate (2.14 g, 18 mmol) were suspended in 10 ml of THF. 1-(2-Chlorophenyl)ethanone (1.4 g, 9 mmol) was gradually added into the reaction flask, maintaining the reaction mixture temperature at 40° C. for 2 h. Then 1 mL of ethanol was added thereto and heated under reflux conditions for 4 h. After cooling, 1 mL of ethanol was added and the mixture was poured onto ice water, and extracted with ether. Ether extracts are combined, washed with water, dried with anhydrous magnesium sulfate, and evaporated. The resulting oil is purified by flash column chromatography (PE/EA=50/1) to afford the title compound (680 mg, 34%) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.24 (3H, t, J=6.8 Hz), 4.03 (2H, s), 4.19 (2H, q, J=6.8 Hz), 7.31-7.36 (2H, m), 7.42-7.45 (2H, m). [M+H] Calc'd for C11H11ClO3, 227; Found, 227.

후처리

  1. temperatureheated under reflux conditions for 4 h
  2. temperatureAfter cooling
  3. additionthe mixture was poured onto ice water
  4. extractionextracted with ether
  5. washwashed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customevaporated
  8. customThe resulting oil is purified by flash column chromatography (PE/EA=50/1)

출처 및 근거

ORD 기록
ord-f0c6a6dd99594fe58aee20fba5547fd6
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987461B2

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