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

HRID 57165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57165
[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-7a919d75d8014fdc879a29588e3a108d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434711B2

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