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

HRID 2405877ノート

反応式

HRID 2405877 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

HCID 177979723-Isopropylthionaphthene

試薬・触媒・溶媒 2

HCID 7964Chlorobenzene溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
136 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-155cab65cfe7456c906e9456707bdabf
出典データセット
uspto-grants-2014_08
特許番号
US08809327B2

反応ノート

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