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

HRID 1691559노트

반응식

HRID 1691559 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

HCID 177979723-Isopropylthionaphthene

시약·촉매·용매 2

HCID 7964Chlorobenzene용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
136 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-e0203beb82a047c0bc1633980c25b48e
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153682B2

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