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Ethylene Glycol → HCID 58812110, Verbindung

HRID 2239986
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2239986
[C:1]1([S:7]([CH2:10][C:11]2[CH:16]=[C:15](F)[CH:14]=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21]([OH:24])[CH2:22][OH:23].CC(C)([O-])C.[K+]>C1COCC1>[C:1]1([S:7]([CH2:10][C:11]2[CH:16]=[C:15]([CH:14]=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])[O:23][CH2:22][CH2:21][OH:24])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 131807962-[(Benzenesulfonyl)methyl]-4-fluoro-1-nitrobenzeneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 58812110HCID 58812110, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 2-benzenesulfonylmethyl-4-fluoro-1-nitrobenzene (10.2 g, 34.7 mmol), ethylene glycol (80 mL, 1.4 mol), and 1 M potassium tert-butoxide in THF (78 mL, 78 mmol) in THF (50 mL) was refluxed under nitrogen for 30 minutes. After cooling to about ambient temperature, the reaction mixture was solvent evaporated. Water was added to the residue, and it was poured into 2.0 N hydrochloric acid and ice. The mixture was then extracted with ethyl acetate and washed with water and brine. The organic phase was dried with anhydrous magnesium sulfate, filtered, concentrated and dried in vacuo at 74° C. for 20 minutes. 2-(3-Benzenesulfonylmethyl-4-nitro-phenoxy)-ethanol as a dark brown gum (11.7 g, 100% yield) was obtained; Mass spectrum (−EI, [M−H]−) m/z 336. 1HNMR (500 MHz, DMSO-d6): δ8.01 (d, 1H, J=9.15 Hz), 7.67-7.73 (m, 1H), 7.54-7.63 (m, 4H), 7.10 (dd, 1H, J=9.51 Hz and 2.93 Hz), 6.85 (d, 1H, J=2.81 Hz), 5.12 (s, 2H), 4.88-4.90 (m, 1H), 3.93-3.96 (m, 2H), 3.65 ppm (d, 2H, J=4.51 Hz). Elemental Analysis for C15H15NO6S: Calcd: C, 53.41; H, 4.48; N, 4.15; Found: C, 53.47; H, 4.69; N, 4.04;

Aufarbeitung

  1. temperaturewas refluxed under nitrogen for 30 minutes
  2. temperatureAfter cooling to about ambient temperature
  3. customevaporated
  4. additionWater was added to the residue, and it
  5. additionwas poured into 2.0 N hydrochloric acid and ice
  6. extractionThe mixture was then extracted with ethyl acetate
  7. washwashed with water and brine
  8. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customdried in vacuo at 74° C. for 20 minutes

Quellen und Nachweise

ORD-Eintrag
ord-0bcaa89b7c37473da90719afdceb2529
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07723329B2

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