tert-Butyl mercaptan → Ethyl 5-(tert-butylsulfanyl)-2,2-dimethyl-4-oxopentanoate
Reaktionsgleichung
O1CCCC1.[CH2:6]([O:8][C:9](=[O:18])[C:10]([CH3:17])([CH3:16])[CH2:11][C:12](=[O:15])[CH2:13]Br)[CH3:7].[CH3:19][C:20]([SH:23])([CH3:22])[CH3:21].C(N(CC)CC)C>CCCCCC>[CH2:6]([O:8][C:9](=[O:18])[C:10]([CH3:17])([CH3:16])[CH2:11][C:12](=[O:15])[CH2:13][S:23][C:20]([CH3:22])([CH3:21])[CH3:19])[CH3:7]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -2.5 °C
Versuchsvorschrift
To a reaction flask containing tetrahydrofuran (5.0-fold, V/W of starting material) was added 5-bromo-2,2-dimethyl-4-oxo-pentanoic acid ethyl ester (1.0 eq) under nitrogen. The mixture was cooled to a temperature of −5-0° C., and a solution of 2-methyl-2-propanethiol (1.2 eq) and triethylamine (1.25 eq) was added while maintaining the temperature below 0° C. The reaction was stirred at room temperature for 25 hours, and then hexane (3.0-fold, V/W of starting material) was slowly added. After agitating for 30 minutes, the solid material was removed by filtration and washed with 50% ethyl acetate/hexane solution. The filtrate was concentrated under reduced pressure to give the desired product, which was taken on to the next step without further purification.
Aufarbeitung
- temperaturewhile maintaining the temperature below 0° C
- stirringAfter agitating for 30 minutes
- customthe solid material was removed by filtration
- washwashed with 50% ethyl acetate/hexane solution
- concentrationThe filtrate was concentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-3f005074dc9648be948a40463512051c
- Quelldatensatz
- uspto-grants-2014_07
- Patentnummer
- US08772495B2
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