Ammonium Chloride → Dimethyl 4,4'-[3-(hydroxymethyl)pentane-1,5-diyl]dibenzoate

HRID 1512199Notizen

Reaktionsgleichung

[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=2)[C:14](O)=[O:15])=[CH:7][CH:6]=1)=[O:4].[Cl-].[NH4+]>C1COCC1.O.C(OCC)(=O)C>[OH:15][CH2:14][CH:13]([CH2:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=1)[CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

At −10° C., 54.1 ml (54.1 mmol) of a 1 M borane/THF complex solution are added dropwise to a solution of 10.4 g (27.1 mmol) of 4-[4-(methoxycarbonyl)phenyl]-2-{2-[4-(methoxycarbonyl)-phenyl]ethyl}butanoic acid in 260 ml of THF. The reaction mixture is then warmed to 0° C. and stirred at this temperature for 4 h. After the reaction has gone to completion, saturated ammonium chloride solution is added, the reaction mixture is diluted with water and ethyl acetate and the aqueous phase is extracted twice with ethyl acetate. The combined organic phases are dried over magnesium sulfate and freed from the solvent under reduced pressure. This gives 8.73 g (23.56 mmol, 87% of theory) of a colorless oil.

Aufarbeitung

additionis added
extractionthe aqueous phase is extracted twice with ethyl acetate
dry with materialThe combined organic phases are dried over magnesium sulfate

Quellen und Nachweise

ORD-Eintrag: ord-a2c698dd2d4d4052a6075d8d97f94147
Quelldatensatz: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08217063B2

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