tert-Butyl mercaptan → Ethyl 5-(tert-butylsulfanyl)-2,2-dimethyl-4-oxopentanoate

HRID 2366090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366090
C1COCC1.[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

6

Edukt 4

HCID 6387tert-Butyl mercaptanHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 4090969Ethyl 5-bromo-2,2-dimethyl-4-oxopentanoate

Produkt 1

HCID 3576811Ethyl 5-(tert-butylsulfanyl)-2,2-dimethyl-4-oxopentanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-2.5 °C

Versuchsvorschrift

To a reaction flask containing THF (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 N2. 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% EtOAc/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

  1. temperaturewhile maintaining the temperature below 0° C
  2. stirringAfter agitating for 30 minutes
  3. customthe solid material was removed by filtration
  4. washwashed with 50% EtOAc/hexane solution
  5. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4f5c98ad0d624c1ab246a3dca2f5a189
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697730B2

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