Pyridine → Ethyl 2-(2-bromopropionyloxy)-ethylcarbamate

HRID 414654

Reaktionsgleichung

Reaktionsgleichung von HRID 414654
[Br:1][CH:2]([CH3:6])[C:3](Br)=[O:4].[OH:7][CH2:8][CH2:9][NH:10][C:11](=[O:15])[O:12][CH2:13][CH3:14].N1C=CC=CC=1>C(OCC)C>[Br:1][CH:2]([CH3:6])[C:3]([O:7][CH2:8][CH2:9][NH:10][C:11](=[O:15])[O:12][CH2:13][CH3:14])=[O:4]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 79047Propanoyl bromide, 2-bromo-HCID 223805ethyl N-(2-hydroxyethyl)carbamate

Produkt 1

HCID 54505068Ethyl 2-(2-bromopropionyloxy)-ethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 32.4 g of 2-bromopropionyl bromide in 70 ml of diethyl ether is added dropwise within one hour while cooling with ice to a solution, cooled to 0° C., of ethyl 2-hyroxyethylcarbamate and 13.1 g of pyridine in 80 ml of diethyl ether. The reaction mixture is then stirred at room temperature for 45 minutes. For the working-up, the mxture is filtered under suction through Celite and the filtrate is poured into water. The aqeuous phase is extracted twice with diethyl ether, and the combined organic phases are washed twice with water and once with saturated sodium chloride solution, dried over anhydrous sodium sulphate and evaporated to dryness. There is obtained ethyl 2-(2-bromopropionyloxy)-ethylcarbamate as a colourless oil which either can be used in the reaction without further purification or can be purified further by chromatography on silica gel with n-hexane/diethyl ether (1:1); nD20 1.4770.

Aufarbeitung

  1. temperaturewhile cooling with ice to a solution
  2. filtrationthe mxture is filtered under suction through Celite
  3. additionthe filtrate is poured into water
  4. extractionThe aqeuous phase is extracted twice with diethyl ether
  5. washthe combined organic phases are washed twice with water and once with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulphate
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-11d59787ad1145b99cf336fae887135a
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04792616

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