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Ethyl Acetoacetate → 3-(2'-Oxo-3'-ethoxycarbonylbutyl)-benzophenone

HRID 1579780
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1579780
[CH3:1][CH2:2][O-:3].[Na+].[Na].[C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=O)C.BrC[C:17]1[CH:18]=[C:19]([CH:28]=[CH:29][CH:30]=1)[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21]>C1C=CC=CC=1>[O:3]=[C:2]([CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:6])[CH2:1][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[C:20]([C:19]1[CH:18]=[CH:17][CH:30]=[CH:29][CH:28]=1)=[O:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8868Ethyl AcetoacetateHCID 895863-(Bromomethyl)benzophenoneHCID 2723922Sodium ethoxideHCID 5360545Sodium

Produkt 1

HCID 214956583-(2'-Oxo-3'-ethoxycarbonylbutyl)-benzophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241Benzene
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Dry sodium ethylate prepared from 2.51 g of sodium was added to 125 ml of anhydrous benzene and 13.5 ml of ethyl acetylacetate at 20°C and after heating at 100°C for 15 minutes, 27.5 g of 3-bromomethyl-benzophenone were added all at once. The reaction mixture was refluxed for 3 hours and after cooling to 20°C, the benzene solution was washed twice with 25 ml of 2N hydrochloric acid and then with water until the wash water was neutral. The solution was dried over sodium sulfate and evaporated to dryness under reduced pressure to obtain 33.8 g of raw product which was chromatographed over silica gel and was eluted with a 50-50 mixture of ether-petroleum ether (B.P. of 40°-60°C) to obtain 15.3 g of 3-(2'-oxo-3'-ethoxycarbonyl-butyl)-benzophenone in the form of a marron resin which was used as is for the next step.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. temperatureafter cooling to 20°C
  3. washthe benzene solution was washed twice with 25 ml of 2N hydrochloric acid
  4. dry with materialThe solution was dried over sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customto obtain 33.8 g of raw product which
  7. customwas chromatographed over silica gel
  8. washwas eluted with a 50-50 mixture of ether-petroleum ether (B.P. of 40°-60°C)

Quellen und Nachweise

ORD-Eintrag
ord-30f4bcb783f145a99570c35c985b9f95
Quelldatensatz
uspto-grants-1976_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03931302

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