Ammonium Chloride → HCID 86649678, Verbindung

HRID 1948784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948784
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].[CH3:10][Si:11]([CH3:21])([CH3:20])[C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O.[Na].[NH4+].[Cl-]>CCO>[N:1]([C:4](=[CH:15][C:14]1[CH:17]=[CH:18][CH:19]=[C:12]([Si:11]([CH3:10])([CH3:21])[CH3:20])[CH:13]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 5360545SodiumHCID 11823172HCID 11823172, Verbindung

Produkt 1

HCID 86649678HCID 86649678, VerbindungAusbeute 26,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A mixture of 31.4 ml (87.5 mmol) of ethyl azidoacetate (at 34% in CH2Cl2) and 3.9 g (21.87 mmol) of 3-trimethylsilylbenzaldehyde prepared according to the procedure described in stage 3.2, diluted in 3 ml of EtOH, is added dropwise to a solution of 2 g (87.5 mmol) of sodium in 30 ml of anhydrous EtOH, maintained under a nitrogen atmosphere and cooled to −10° C. The reaction mixture is stirred at 0° C. for 4 h. It is subsequently hydrolysed by adding, with vigorous stirring, 100 ml of an aqueous solution of NH4Cl (30%). The aqueous phase is extracted with 3×50 ml of EtOAc. The combined organic phases are washed with water, dried over Na2SO4 and concentrated under reduced pressure. The reaction crude is purified by silica gel column chromatography, elution being carried out with an isocratic mixture of heptane and CH2Cl2 (80/20). 1.7 g of the expected ethyl 2-azido-3-(3-trimethylsilylphenyl)propenoate are thus isolated in the form of a yellow oil.

Aufarbeitung

  1. customprepared
  2. temperaturemaintained under a nitrogen atmosphere
  3. extractionThe aqueous phase is extracted with 3×50 ml of EtOAc
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe reaction crude
  8. customis purified by silica gel column chromatography, elution
  9. additionbeing carried out with an isocratic mixture of heptane and CH2Cl2 (80/20)

Quellen und Nachweise

ORD-Eintrag
ord-3afacf1df990473d8d563892e941e2ac
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399491B2

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