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Water → Methyl 2-chloro-3-oxoheptanoate

HRID 1983551
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1983551
[CH3:1][O:2][C:3](=[O:11])[CH2:4][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9].S(Cl)([Cl:15])(=O)=O.O>ClCCl>[CH3:1][O:2][C:3](=[O:11])[CH:4]([Cl:15])[C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 546075Methyl 3-oxoheptanoate

Produkt 1

HCID 57713025Methyl 2-chloro-3-oxoheptanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5.0 g 3-Oxo-heptanoic acid methyl ester were dissolved in 80 ml dry dichloromethane and 2.82 ml sulfurylchloride were added. The reaction mixture was stirred at room temperature for 30 minutes. 20 ml of water were added and the reaction mixture extracted five times with portions of 30 ml of dichloromethane. The combined organic extracts were washed with water and saturated NaHCO3 solution and brine and dried over MgSO4. The solvent was removed under reduced pressure to obtain 6.0 g 2-Chloro-3-oxo-heptanoic acid methyl ester as raw material. This material was used without further purification. 6.0 g 2-Chloro-3-oxo-heptanoic acid methyl ester were dissolved in 50 ml ethanol and 6.4 g 4-(Trifluoromethyl)thiobenzamide were added. The reaction mixture was heated under reflux overnight. The solvent was removed under reduced pressure and the residue purified by chromatography with the eluent n-heptane:ethyl acetate=100:1=>60:1. This gives 7.4 g 4-Butyl-2-(4-trifluoromethylphenyl)-thiazol-5- carboxylic acid methyl ester as yellow oil.

Aufarbeitung

  1. extractionthe reaction mixture extracted five times with portions of 30 ml of dichloromethane
  2. washThe combined organic extracts were washed with water and saturated NaHCO3 solution and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-91c239f6b9ba45b6a40b7928487e8548
Quelldatensatz
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07541464B2

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