Tributyltin Chloride → Tributyl[5-(1,3-dioxolan-2-yl)4-methylthien-2-yl]stannane

HRID 9656

Reaktionsgleichung

Reaktionsgleichung von HRID 9656
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[O:11][CH2:10][CH2:9][O:8]1.C([Li])CCC.[CH2:17]([Sn:21](Cl)([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20]>O1CCCC1.C(OCC)C>[CH2:26]([Sn:21]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:22][CH2:23][CH2:24][CH3:25])[C:5]1[S:4][C:3]([CH:7]2[O:11][CH2:10][CH2:9][O:8]2)=[C:2]([CH3:1])[CH:6]=1)[CH2:27][CH2:28][CH3:29]

Komponenten

6

Edukt 3

HCID 15096Tributyltin ChlorideHCID 129265222-(3-Methylthiophen-2-yl)-1,3-dioxolane2×HCID 178418339Butyllithium

Produkt 1

HCID 21986287Tributyl[5-(1,3-dioxolan-2-yl)4-methylthien-2-yl]stannane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

A mixture of 2-(3-methylthien-2-yl)-1,3-dioxolane (intermediate 75, 1.5 g) in tetrahydrofuran (50 ml), stirred at −60° C. under a nitrogen atmosphere, was treated drop-wise with 1.6M n-butyl lithium in hexanes (6.1 ml). The reaction mixture was stirred at this temperature for 1 hour and tributyltin chloride (2.6 ml) was added; stirring was continued at −60° C. for 1 hour and then the reaction allowed to warm to ambient temperature. After 18 hours the reaction mixture was diluted with diethylether and this mixture was extracted with water and the ether layer dried with brine and over magnesium sulfate. The product isolated after evaporation of the solvent was further purified by flash column chromatography using cyclohexane:ethyl acetate (50:1) as eluent to give the title compound as a yellow oil.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at this temperature for 1 hour
  2. stirringstirring
  3. temperatureto warm to ambient temperature
  4. extractionthis mixture was extracted with water
  5. dry with materialthe ether layer dried with brine and over magnesium sulfate
  6. customThe product isolated
  7. customafter evaporation of the solvent
  8. customwas further purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bdd6a74b4fde4fe1a64ca556ea6560a2
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091237B2

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