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

HRID 2075196

反応式

HRID 2075196 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9e93489e2ba24216ba1a38a670f8f30e
出典データセット
uspto-grants-2011_04
特許番号
US07919519B2

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