tert-Butyl mercaptan → Ethyl 4-(tert-butylthio)-3-oxobutanoate

HRID 1948887

Reaktionsgleichung

Reaktionsgleichung von HRID 1948887
Cl[CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:11][C:12]([SH:15])([CH3:14])[CH3:13].C(N(CC)CC)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][C:3](=[O:10])[CH2:2][S:15][C:12]([CH3:14])([CH3:13])[CH3:11])[CH3:9]

Komponenten

6

Edukt 3

HCID 6387tert-Butyl mercaptanHCID 8471TriethylamineHCID 69484Ethyl 4-chloroacetoacetate

Produkt 1

HCID 10465978Ethyl 4-(tert-butylthio)-3-oxobutanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl 4-chloroacetoacetate (7.5 mL, 51.9 mmol), 2-methyl-2-propanethiol (5.6 mL, 49.7 mmol), triethylamine (10.8 mL, 77.4 mmol), and catalytic tetrabutylammonium bromide were dissolved in THF (250 mL) and stirred at room temperature overnight. Silica gel was added, and the mixture was concentrated and filtered over a plug of silica gel to obtain the desired product (B-1), which was used without further purification.

Aufarbeitung

  1. additionSilica gel was added
  2. concentrationthe mixture was concentrated
  3. filtrationfiltered over a plug of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5ec9328f963847768482c3c278621ee9
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399666B2

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