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

HRID 2075196

Reaction equation

HRID 2075196 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9e93489e2ba24216ba1a38a670f8f30e
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Linked notes

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