Tributyltin Chloride → HCID 59155833, Verbindung

HRID 1662880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662880
[CH2:1]([O:3][P:4]([C:9]1[CH:13]=[CH:12][S:11][CH:10]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C([Li])CCC.[CH2:19]([Sn:23](Cl)([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH3:22].P([O-])([O-])(O)=O.[Na+].[Na+].P([O-])(O)(O)=O.[Na+]>C1COCC1>[CH2:28]([Sn:23]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:24][CH2:25][CH2:26][CH3:27])[C:10]1[S:11][CH:12]=[CH:13][C:9]=1[P:4]([O:6][CH2:7][CH3:8])([O:3][CH2:1][CH3:2])=[O:5])[CH2:29][CH2:30][CH3:31]

Komponenten

6

Edukt 4

HCID 15096Tributyltin ChlorideHCID 153633033-(Diethoxyphosphoryl)thiopheneHCID 86630341Sodium phosphate (Na3(PO4)2)HCID 178418339Butyllithium

Produkt 1

HCID 59155833HCID 59155833, VerbindungAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

In THF, 1.96 g (8.90 mmols) of 3-(diethoxyphosphoryl)thiophene was dissolved and cooled down to −78° C. Commercially available n-butyl lithium (1.59 M hexane solution, 8.90 mmols) was slowly dropped, followed by stirring for 3 hours at a standing temperature. Thereafter, 3.19 g (9.80 mmols) of commercially available tributylstannyl chloride was dropped and stirred for 1.5 hours. After completion of the reaction, a disodium hydrogen phosphate/sodium dihydrogen phosphate buffer solution, adjusted to pH=7, was added so as to complete the reaction, followed by extraction with ethyl acetate. The organic phase was washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was removed, and the resulting crude product was purified with a silica gel column (ethyl acetate:hexane=1:2) to obtain the specified substance in the form of a transparent oil at a yield of 4.35 g (yield: 96%). The thus obtained substance was used as it is for reaction in Example 12(3).

Aufarbeitung

  1. stirringstirred for 1.5 hours
  2. customAfter completion of the reaction
  3. additionwas added so as
  4. customthe reaction
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic phase was washed with a saturated saline solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed
  9. customthe resulting crude product was purified with a silica gel column (ethyl acetate:hexane=1:2)
  10. customto obtain the specified substance in the form of a transparent oil at a yield of 4.35 g (yield: 96%)
  11. customis for reaction in Example 12(3)

Quellen und Nachweise

ORD-Eintrag
ord-c9a430d1939e453c9667a1d2df11abd2
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030438B2

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