3-Methyl-1-phenylsulfanyl-butan-2-one → 3-Isopropylthionaphthene

HRID 2405877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2405877
[CH3:1][CH:2]([CH3:13])[C:3](=O)[CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClC1C=CC=CC=1.CCOC(C)=O>[CH:2]([C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][CH:4]=1)([CH3:13])[CH3:1]

Komponenten

4

Edukt 1

HCID 5512653-Methyl-1-phenylsulfanyl-butan-2-one

Produkt 1

HCID 177979723-Isopropylthionaphthene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7964ChlorobenzeneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
136 °C

Versuchsvorschrift

To a hot solution (136° C.) of PPA (8.2 g) in chlorobenzene (50 mL) is added a solution of compound 563-C (4.34 g; 22.4 mmol) in chlorobenzene (35 mL). The reaction was stirred at 136° C. for 18 h, cooled to ambient temperature, diluted with EtOAc, quenched with H2O, and the EtOAc layer was washed with H2O, brine, dried over Na2SO4, filtered and the solvent evaporated under reduced pressure. The crude residue was purified by flash column chromatography (SiO2), eluting with a heptane-EtOAc gradient to afford compound 563-D as an oil. 1H-NMR (DMSO-d6): δ 1.31-1.33 (d, 6H), 3.26-3.31 (m, 1H), 7.33-7.43 (m, 2H), 7.83-7.85 (m, 1H), 7.95-7.97 (m, 1H); MS: m/z 328.0 (MH+).

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. customquenched with H2O
  3. washthe EtOAc layer was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude residue was purified by flash column chromatography (SiO2)
  8. washeluting with a heptane-EtOAc gradient
  9. customto afford compound 563-D as an oil

Quellen und Nachweise

ORD-Eintrag
ord-155cab65cfe7456c906e9456707bdabf
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809327B2

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