Triethylamine → Benzofuran-5-yl(phenyl)methanone

HRID 2075192

Reaktionsgleichung

Reaktionsgleichung von HRID 2075192
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[OH:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.C(N(CC)CC)C.C(Cl)Cl.CS(C)=O>CS(C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 21912085Dimethylsulfoxide-dichloromethaneHCID 58415371Benzofuran-5-yl(phenyl)methanol

Produkt 1

HCID 58415352Benzofuran-5-yl(phenyl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of benzofuran-5-yl(phenyl)methanol (4.0 g, 18 mmol) and triethylamine (7.3 mL, 54 mmol) in 30 mL 1:1 DCM/DMSO under nitrogen at 0° C. was added a solution of SO3*py (8.5 g, 54 mmol) in 20 mL DMSO dropwise via addition funnel. The reaction was allowed to stir 5 h at 0° C. and was quenched by addition of water and 250 mL Et2O. The organic layer was washed with water, 1N HCl, 1N NaOH, brine, and was dried over sodium sulfate, filtered, and concentrated. The resulting solid benzofuran-5-yl(phenyl)methanone was used without further purification. MS (ESI) m/z: Calculated: 222.1; Observed: 223.0 (M++1).

Aufarbeitung

  1. additiondropwise via addition funnel
  2. customwas quenched by addition of water and 250 mL Et2O
  3. washThe organic layer was washed with water, 1N HCl, 1N NaOH, brine
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting solid benzofuran-5-yl(phenyl)methanone was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-770de3bda5be496e98d3f55f52d5696b
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919519B2

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