1-Bromo-4-chlorobutane → Ethyl 6-chloro-2-ethoxycarbonyl-2-(p-toluoylamino)hexanoate

HRID 890660ノート

反応式

HRID 890660 の反応式
[Na].[C:2]1([CH3:22])[CH:7]=[CH:6][C:5]([C:8]([NH:10][CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:9])=[CH:4][CH:3]=1.Br[CH2:24][CH2:25][CH2:26][CH2:27][Cl:28]>C(O)C>[Cl:28][CH2:27][CH2:26][CH2:25][CH2:24][C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])([NH:10][C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:22])=[CH:3][CH:4]=1)=[O:9])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

参加物

5

反応物 3

HCID 813641-Bromo-4-chlorobutaneHCID 5360545SodiumHCID 17447783Diethyl p-toluoylaminomalonate

生成物 1

HCID 21866781Ethyl 6-chloro-2-ethoxycarbonyl-2-(p-toluoylamino)hexanoate収率 54.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Sodium (6.42 g) was dissolved in 390 ml of ethanol at room temperature. To the solution was added 78.0 g of diethyl p-toluoylaminomalonate, and 47.9 g of 1-bromo-4-chlorobutane was added dropwise under heating to reflux. The mixture was heated to reflux for 20 hours. The reaction solution was concentrated. To the residue was added water, and the mixture was washed with ethyl acetate. After washing with 10% hydrochloric acid and water sequentially, the solution was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=9:1) to provide 55.7 g of the objective compound as colorless oil.

後処理

  1. additionwas added dropwise
  2. temperatureunder heating to reflux
  3. temperatureThe mixture was heated
  4. temperatureto reflux for 20 hours
  5. concentrationThe reaction solution was concentrated
  6. additionTo the residue was added water
  7. washthe mixture was washed with ethyl acetate
  8. washAfter washing with 10% hydrochloric acid and water sequentially
  9. dry with materialthe solution was dried over anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=9:1)

出典と根拠

ORDレコード
ord-8ade23e08b5f4b56a4323c7c7e83f1b6
出典データセット
uspto-grants-2006_02
特許番号
US06998412B2

反応ノート

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