Tin tetrachloride → HCID 86702351, Verbindung

HRID 2172542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2172542
[CH:1]([S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)SC1C=CC=CC=1.[Sn](Cl)(Cl)(Cl)Cl.[C:28]1([O:38][Si](C)(C)C)[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][CH2:30][CH:29]=1>ClCCl>[C:17]1([S:16][CH:1]([S:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:29]2[CH2:30][CH2:31][C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:28]2=[O:38])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

5

Edukt 3

HCID 24287Tin tetrachlorideHCID 615706Tris(phenylthio)methaneHCID 4245325(3,4-Dihydro-1-naphthyloxy)trimethylsilane

Produkt 1

HCID 86702351HCID 86702351, VerbindungAusbeute 64,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

Under argon, 6.22 g (23.8 mmol) of triphenyl trithioorthoformate (1,1′,1″-(methanetriyltrisulphanediyl)dibenzene) are dissolved in anhydrous dichloromethane and cooled to −70° C. 23.8 ml (23.8 mmol) of tin(IV) tetrachloride solution (1 M in dichloromethane) and 5.73 g (26.3 mmol) of (3,4-dihydronaphthalen-1-yloxy)trimethylsilane are added in succession, and the mixture is stirred at −70° C. for 40 min. The reaction mixture is poured into ice-water and extracted with dichloromethane. After washing with water, the organic phase is dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate) gives 5.80 g of 2-[bis(phenylsulphanyl)methyl]-3,4-dihydronaphthalen-1(2H)-one.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washAfter washing with water
  3. dry with materialthe organic phase is dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-46e42e0298d24abe8a8d2274acb4a94f
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09055743B2

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