Diisopropylamine → 5-Hexenoic acid, 2-[(phenylmethylene)amino]-, methyl ester

HRID 232584

Reaktionsgleichung

Reaktionsgleichung von HRID 232584
C(NC(C)C)(C)C.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[CH3:13][O:14][C:15](=[O:25])[CH2:16][N:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.BrCCC=C>O1CCCC1.CCCCCC.O>[CH3:13][O:14][C:15](=[O:25])[CH:16]([CH2:11][CH2:10][CH:9]=[CH2:8])[N:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

8

Edukt 4

HCID 7912DiisopropylamineHCID 21241Homoallyl bromideHCID 4169153Methyl [(phenylmethylidene)amino]acetateHCID 178418339Butyllithium

Produkt 1

HCID 120394615-Hexenoic acid, 2-[(phenylmethylene)amino]-, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Dissolve diisopropylamine (15.4 mL, 110 mmol) in tetrahydrofuran (250 mL), place under a nitrogen atmosphere and cool to -78° C. Add n-butyllithium (39 mL of a 2.7M solution in hexane, 105 mmol). Stir for 30 minutes and add, by dropwise addition, a solution of N-(phenylmethylene)glycine methyl ester (17.7 g, 100 mmol) in tetrahydrofuran (25 mL). Stir for 15 minutes and add 4-bromobutene (13.5 g, 100 mmol) and allow to warm slowly to room temperature. Add hexamethylphosmhoramide (20 mL, 100 mmol) and stir under a nitrogen atmosphere for 3 hours. Pour into water, extract into ethyl ether and wash with brine several times. Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound as an amber oil (25 g).

Aufarbeitung

  1. additionadd, by dropwise addition
  2. stirringStir for 15 minutes
  3. temperatureto warm slowly to room temperature
  4. additionAdd hexamethylphosmhoramide (20 mL, 100 mmol)
  5. stirringstir under a nitrogen atmosphere for 3 hours
  6. extractionextract into ethyl ether
  7. washwash with brine several times
  8. dry with materialDry (MgSO4)
  9. customevaporate the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5308dafe4381411eb935739ffe65272a
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591739

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