Réaction #164679

ord-e4500a20d89a4aafa3a9db98fd3661f1

Équation de réaction

CCOC(=O)CC(=O)CCl
Ethyl 4-chloroacetoacetate
CC(C)(C)S
2-methyl-2-propanethiol
CCN(CC)CC
triethylamine
CCOC(=O)CC(=O)CSC(C)(C)C
desired product
CCOC(=O)CC(=O)CSC(C)(C)C
4-tert-Butylsulfanyl-3-oxo-butyric acid ethyl ester

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONSilica gel was added
  2. 2
    Concentrationthe mixture was concentrated
  3. 3
    Filtrationfiltered over a plug of silica gel

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08841295B2uspto-grants-2014_09