Ethoxalyl chloride → HCID 66880855, Verbindung

HRID 1844534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844534
Cl[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:13][O:14][CH2:15][CH2:16][S:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[CH2:6]([O:5][C:3](=[O:4])[C:2]([C:21]1[CH:22]=[CH:23][C:18]([S:17][CH2:16][CH2:15][O:14][CH3:13])=[CH:19][CH:20]=1)=[O:8])[CH3:7]

Komponenten

5

Edukt 3

HCID 20884Ethoxalyl chlorideHCID 40561742-METHOXYETHYL PHENYL SULFIDEHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 66880855HCID 66880855, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ethyl chloroglyoxylate (8.76 mL) was added dropwise to a suspension of aluminum chloride (13.2 g, crushed) in methylene chloride (127 mL) under stirring and cooling with ice, and (2-methoxyethyl)phenylsulfide (12.0 g) was added dropwise thereto. The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice water (200 mL), and the mixture was stirred for 10 minutes. The organic layer was separated, washed with a saturated aqueous sodium hydrogen carbonate solution (40 mL×3), and washed with saturated brine (60 mL). The washed organic layer was dried over anhydrous sodium sulfate, filtrated, and evaporated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, hexane:ethyl acetate=4:1) to give 2-[4-(2-methoxyethylthio)phenyl]-2-oxoacetic acid ethyl ester (1.98 g).

Aufarbeitung

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. stirringthe mixture was stirred for 10 minutes
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous sodium hydrogen carbonate solution (40 mL×3)
  6. washwashed with saturated brine (60 mL)
  7. dry with materialThe washed organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltrated
  9. customevaporated under reduced pressure
  10. customThe obtained residue was purified by column chromatography (silica gel, hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-9a86842437eb420f9dabc433690f8d81
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946440B2

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