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

HRID 1172909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172909
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-026d52a76ea84f1d8a59b57ba3926bbd
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834037B2

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