Tin tetrachloride → HCID 69412293, Verbindung

HRID 1373880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373880
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]3[S:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[CH:18]=3)[CH:13]=2)[C:8]=1[Cl:26])[CH3:2].[C:28](Cl)(=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32].[Sn](Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]3[S:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[C:18]=3[C:28](=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32])[CH:13]=2)[C:8]=1[Cl:26])[CH3:2]

Komponenten

5

Edukt 3

HCID 24287Tin tetrachlorideHCID 61186Valeryl chlorideHCID 69411210HCID 69411210, Verbindung

Produkt 1

HCID 69412293HCID 69412293, VerbindungAusbeute 2,14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

A mixture of yielded (6-benzo[b]thiophen-2-yl-1-chloro-naphthalen-2-yloxy)-acetic acid ethyl ester (2.7 g, 6.8 mmol), valeryl chloride (3.9 mL, 33 mmol) in four portions and tin (IV) chloride (6.4 mL, 56 mmol)in four portions in chloroform (55 mL) was refluxed for five hours. It was then allowed to cool to ambient temperature and poured into ice water. It was diluted with additional chloroform and washed with water and brine. It was then dried with anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was purified three times by flash chromatography (Biotage apparatus) using (1) 25–60% methylene chloride in hexane, (2) 20–40% 1,2-dichloroethane in hexane and (3) 2.5–7.5% methyl t-butyl ether in hexane. It was then purified by HPLC using 92% acetonitrile (0.1% trifluoroacetic acid) in water as the mobile phase. Evaporating the solvent and extracting with ethyl acetate, washing with water and brine, drying with anhydrous magnesium sulfate, filtering, concentrating and drying in vacuo at 60° C. for 20 minutes yielded [1-chloro-6-(3-pentanoyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester as an olive gum (0.0702 g, 2.14%).

Aufarbeitung

  1. temperaturewas refluxed for five hours
  2. washwashed with water and brine
  3. dry with materialIt was then dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customThe residue was purified three times by flash chromatography (Biotage apparatus)
  7. customIt was then purified by HPLC
  8. customEvaporating the solvent
  9. extractionextracting with ethyl acetate
  10. washwashing with water and brine
  11. dry with materialdrying with anhydrous magnesium sulfate
  12. filtrationfiltering
  13. concentrationconcentrating
  14. customdrying in vacuo at 60° C. for 20 minutes

Quellen und Nachweise

ORD-Eintrag
ord-5de67586807e4dbc9ea5c7eefc9ca677
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07163954B2

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