Potassium Carbonate → 3-[2-(4-Thiomorpholinyl)ethoxy]benzaldehyde

HRID 619191

Reaktionsgleichung

Reaktionsgleichung von HRID 619191
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9].C([O-])([O-])=O.[K+].[K+].[NH:19]1[CH2:24][CH2:23][S:22][CH2:21][CH2:20]1>CN(C=O)C>[N:19]1([CH2:2][CH2:3][O:4][C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=2)[CH:8]=[O:9])[CH2:24][CH2:23][S:22][CH2:21][CH2:20]1

Komponenten

5

Edukt 3

HCID 11430Potassium Carbonate2×HCID 67164Thiomorpholine2×HCID 27355653-(2-Bromoethoxy)benzaldehyde

Produkt 1

HCID 218461173-[2-(4-Thiomorpholinyl)ethoxy]benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-(2-bromoethoxy)benzaldehyde (3.91 g, 17.07 mmol), K2CO3 (3.1 g), thiomorpholine (1.9 ml) and DMF (30 ml) was warmed on a steambath overnight. Additional K2CO3 (0.7 g) and thiomorpholine (1.0 ml) were added and the reaction mixture was warmed on a steam bath overnight. The reaction mixture was cooled to room temperature, filtered and the filtrate was stripped to afford an amber oil. The oil was combined with the product from a similar experimental run and purified by column chromatography on silica gel eluting with EtOAc (100%) to afford, as an oil, 3-[2-(4-thiomorpholinyl)ethoxy]benzaldehyde.

Aufarbeitung

  1. temperaturewas warmed on a steambath overnight
  2. temperaturethe reaction mixture was warmed on a steam bath overnight
  3. filtrationfiltered
  4. customto afford an amber oil
  5. custompurified by column chromatography on silica gel eluting with EtOAc (100%)

Quellen und Nachweise

ORD-Eintrag
ord-745f02414d9e4e17928a7371debf8e01
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958929

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