Acetic Acid → 5-(2-Phenyl-1,3-dithiolan-2-yl)benzofuran

HRID 2075196

반응식

HRID 2075196 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=O)=[CH:9][C:4]=2[CH:3]=[CH:2]1.C(O)(=O)C.[CH2:22]([SH:25])[CH2:23][SH:24].B(F)(F)F>C(Cl)Cl>[C:12]1([C:10]2([C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH:2]=[CH:3][C:4]=4[CH:9]=3)[S:25][CH2:22][CH2:23][S:24]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 6356Boron trifluorideHCID 109021,2-EthanedithiolHCID 58415352Benzofuran-5-yl(phenyl)methanone

생성물 1

HCID 584153375-(2-Phenyl-1,3-dithiolan-2-yl)benzofuran

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of benzofuran-5-yl(phenyl)methanone (2.45 g, 11.0 mmol), glacial acetic acid (1.27 mL, 22.0 mmol) and 1,2-ethanedithiol (1.39 mL, 16.5 mmol) in 30 mL DCM at ambient temperature was added boron trifluoride diethyletherate (1.38 mL, 11.0 mmol). The reaction was allowed to stir overnight, and was quenched by the addition of 1N NaOH. The aq. layer was extracted 1×DCM, and the combined organics were dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography, ISCO, 0-20% EtOAc/hexanes provided 5-(2-phenyl-1,3-dithiolan-2-yl)benzofuran as a clear/colorless oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.99 (d, J=2.0 Hz, 1H), 7.84 (d, J=2.0 Hz, 1H), 7.48-7.57 (m, 3H), 7.38-7.45 (m, 1H), 7.29-7.36 (m, 2H), 7.24 (t, J=7.3 Hz, 1H), 6.96 (d, J=2.0 Hz, 1H) 3.43 (s, 4H).

후처리

  1. customwas quenched by the addition of 1N NaOH
  2. extractionThe aq. layer was extracted 1×DCM
  3. dry with materialthe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography, ISCO, 0-20% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-9e93489e2ba24216ba1a38a670f8f30e
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919519B2

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