Water → Tert-butyl {2-[4-chloro-3-cyano-6-(1-hydroxyethyl)-2-vinylphenoxy]ethyl}carbamate
Reaktionsgleichung
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[C:8]([CH:21]=[CH2:22])[C:7]([C:23]#[N:24])=[C:6]([Cl:25])[CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].O>CO>[Cl:25][C:6]1[CH:5]=[C:4]([CH:1]([OH:3])[CH3:2])[C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[C:8]([CH:21]=[CH2:22])[C:7]=1[C:23]#[N:24]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Tert-butyl [2-(6-acetyl-4-chloro-3-cyano-2-vinylphenoxy)ethyl]carbamate (1.6 g, 4.4 mmol) was dissolved in methanol (40 mL) cooled in an ice bath and the sodium tetrahydroborate (0.16 g, 4.4 mmol) was added. The reaction was stirred for 1 h and water was added to quench residual hydride and the reaction was concentrated to remove the methanol. The aqueous was diluted with ethyl acetate washed with brine, dried over magnesium sulfate and concentrated to give tert-butyl {2-[4-chloro-3-cyano-6-(1-hydroxyethyl)-2-vinylphenoxy]ethyl}carbamate as a glass (1.6 g, 100%). LCMS calculated for C18H23ClN2O4Na (M+Na)+: m/z=389.1; found: 389.1.
Aufarbeitung
- temperaturecooled in an ice bath
- customto quench residual hydride
- concentrationthe reaction was concentrated
- customto remove the methanol
- additionThe aqueous was diluted with ethyl acetate
- washwashed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-985d1c5a7ed945d7bca61e995a8354a8
- Quelldatensatz
- uspto-grants-2016_04
- Patentnummer
- US09309251B2
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