Sulfuric Acid → 1-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanone

HRID 898134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898134
[CH2:1]([S:7][C:8]1[N:13]=[C:12]([CH:14]([OH:16])[CH3:15])[CH:11]=[C:10]([CH3:17])[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.OS(O)(=O)=O>CC(C)=O>[CH2:1]([S:7][C:8]1[N:13]=[C:12]([C:14](=[O:16])[CH3:15])[CH:11]=[C:10]([CH3:17])[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 692907201-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanolHCID 131709961Jones' reagent

Produkt 1

HCID 692927551-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanoneAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

1-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanol (2.2 g, 8.65 mmol) was dissolved under nitrogen in acetone (20 mL). Then 2 M Jones' reagent prepared from 20 g CrO3 in 100 mL 4 M H2SO4 (6.5 mL, 13 mmol) was add dropwise. After stirring for 2 h at 20° C., the resulting green solution was decanted from the chromium salts and extracted with AcOEt and sat. NaCl solution. The crude product was purified by chromatography on silica gel with a heptane/AcOEt gradient. One obtained 960 mg (44 %) of white crystals. MS: m/z=252 (M).

Aufarbeitung

  1. additionwas add dropwise
  2. customthe resulting green solution was decanted from the chromium salts
  3. extractionextracted with AcOEt and sat. NaCl solution
  4. customThe crude product was purified by chromatography on silica gel with a heptane/AcOEt gradient

Quellen und Nachweise

ORD-Eintrag
ord-203a9b8813974ef6b56ea1e9bbf0b63d
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351700B2

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