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Chloroform → HCID 53703941, Verbindung

HRID 1701166
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1701166
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:16]([CH2:18][C:19]([OH:21])=[O:20])=[O:17])[CH3:15])=[CH:10][CH:9]=1.[OH-].[K+].[CH:24](Cl)(Cl)Cl.CI>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:24][O:20][C:19](=[O:21])[CH2:18][S:16]([CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[CH:9][CH:10]=1)[CH3:15])=[O:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6212ChloroformHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 20348737HCID 20348737, Verbindung

Produkt 1

HCID 53703941HCID 53703941, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium Iodide
Katalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

1.1 gm (3 millimols) of tetrabutylammonium iodide and 3.06 gm (10 millimols) of [1-(2'-fluoro-4-biphenylyl)-ethylsulfinyl]-acetic acid (m.p. 164°-165° C.) were added to a solution of 730 mgm (13 millimols) of potassium hydroxide in 20 ml of water, then 20 ml of chloroform and 2 ml of methyl iodide were added, and the mixture was stirred at room temperature for 10 hours. Afterwards, the organic phase was separated from the neutral aqueous phase, washed with dilute hydrochloric acid and then with water, dried and evaporated. The residue (3.6 gm) was purified by chromatography on 100 gm of silicagel (grain size: 0.05-0.2 mm) with cyclohexane ethyl acetate=1/4. After evaporation of the combined fractions with an Rf -value of 0.4 and recrystallization of the residue from isopropanol, 1.7 gm (53% of theory) of the title compound m.p. 75°-77° C. were obtained.

Aufarbeitung

  1. customAfterwards, the organic phase was separated from the neutral aqueous phase
  2. washwashed with dilute hydrochloric acid
  3. dry with materialwith water, dried
  4. customevaporated
  5. customThe residue (3.6 gm) was purified by chromatography on 100 gm of silicagel (grain size: 0.05-0.2 mm) with cyclohexane ethyl acetate=1/4
  6. customAfter evaporation of the combined fractions
  7. customwith an Rf -value of 0.4 and recrystallization of the residue from isopropanol, 1.7 gm (53% of theory) of the title compound m.p. 75°-77° C.
  8. customwere obtained

Quellen und Nachweise

ORD-Eintrag
ord-5b279a8695ed460f8018d6edb9b30545
Quelldatensatz
uspto-grants-1980_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04191776

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