Ethanol → Ethyl (2-chlorobenzoyl)acetate

HRID 878487

反応式

HRID 878487 の反応式
[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]

参加物

6

反応物 4

HCID 702Ethanol2 回HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 72864Ethanone, 1-(2-chlorophenyl)-

生成物 1

HCID 292405Ethyl (2-chlorobenzoyl)acetate収率 34%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f0c6a6dd99594fe58aee20fba5547fd6
出典データセット
uspto-grants-2015_03
特許番号
US08987461B2

関連ノート

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