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

HRID 2405877Notes

Reaction equation

HRID 2405877 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

HCID 177979723-Isopropylthionaphthene

Reagents, catalysts & solvents 2

HCID 7964ChlorobenzeneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
136 °C

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-155cab65cfe7456c906e9456707bdabf
Source dataset
uspto-grants-2014_08
Patent number
US08809327B2

Reaction notes

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