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

HRID 260330

Reaktionsgleichung

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.CN(C)P(N(C)C)(N(C)C)=O>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

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 (13.4 g, 100 mmol) and allow to warm slowly to room temperature. Add hexamethylphosphoramide (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

additionadd, by dropwise addition
stirringStir for 15 minutes
temperatureto warm slowly to room temperature
extractionextract into ethyl ether
washwash with brine several times
dry with materialDry (MgSO4)
customevaporate the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-dee5893d9e76430ba5f39b6ebd3ce9ea
Quelldatensatz: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05527795

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