Ethylene Glycol → 2-(4-Bromothiophen-2-yl)-1,3-dioxolane

HRID 458413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 458413
C1C=CC=CC=1.[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[O:14])[S:11][CH:12]=1.[CH2:15](O)[CH2:16][OH:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC.O>[Br:7][C:8]1[CH:9]=[C:10]([CH:13]2[O:17][CH2:16][CH2:15][O:14]2)[S:11][CH:12]=1

Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 877924-Bromothiophene-2-carbaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 38572552-(4-Bromothiophen-2-yl)-1,3-dioxolaneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A benzene (55 mL) solution of 4-bromo-2-thiophene carboxaldehyde (9.76 g 51.09 mmol), ethylene glycol (8.55 mL, 153.26 mmol) and p-toluenesulfonic acid monohydrate (0.972 g, 5.11 mmol) was refluxed with azeotropic removal of H2O for 6 h and then cooled to ambient temperature. The reaction mixture was diluted with Et2O and the organics washed with sat'd NaHCO3, brine and then dried (MgSO4), filtered and concentrated. Chromatography on silica gel using 95:5 Hexanes:EtOAc eluted the product to provide the title compound upon concentration as a yellow oil (10.76 g 90% yield): 1H NMR (CDCl3, 400 MHz) δ 7.22 (s, 1H), 7.08 (s, 1H), 6.07 (s, 1H), 4.14–4.00 (m, 4H).

Aufarbeitung

  1. washthe organics washed with sat'd NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washChromatography on silica gel using 95:5 Hexanes:EtOAc eluted the product

Quellen und Nachweise

ORD-Eintrag
ord-b38d458893a746409b3db3f851fa7406
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189851B2

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