Hexane → 4-(1,3-Dioxolan-2-yl)-5-tributylstannylthiazole

HRID 6825

Reaktionsgleichung

Reaktionsgleichung von HRID 6825
Br[C:2]1[S:3][CH:4]=[C:5]([CH:7]2[O:11][CH2:10][CH2:9][O:8]2)[N:6]=1.C([Li])CCC.CCCCCC.[CH2:23]([Sn:27](Cl)([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH3:26]>C1COCC1.O>[O:8]1[CH2:9][CH2:10][O:11][CH:7]1[C:5]1[N:6]=[CH:2][S:3][C:4]=1[Sn:27]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 15096Tributyltin ChlorideHCID 219522862-Bromo-4-(1,3-dioxolan-2-yl)thiazoleHCID 178418339Butyllithium

Produkt 1

HCID 219520694-(1,3-Dioxolan-2-yl)-5-tributylstannylthiazoleAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Bromo-4-(1,3-dioxolan-2-yl) thiazole (6.4 g ,27.14 mmol) was stirred at −78° C. in dry THF (38 ml). 1.6M n butyl lithium in hexane (18.6 ml, 29.78 mmol) was added dropwise under nitrogen. After 30 min at this temperature, tributyl tin chloride (7.35 ml, 27.14 mmol) was added dropwise. The reaction was allowed to warm to 0° and water (20 ml) was added. The product was extracted into ether (3×100 ml). The combined organic extracts were dried (MgSO4 ) and evaporated. The residue was triturated with isohexane (3×100 ml) and the mother liquors were decanted, combined and concentrated to give a brown oil (11.88 g); m/z 444–450.

Aufarbeitung

  1. temperatureto warm to 0°
  2. extractionThe product was extracted into ether (3×100 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4 )
  4. customevaporated
  5. customThe residue was triturated with isohexane (3×100 ml)
  6. customthe mother liquors were decanted
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8f9cade0188a4427a37fc2196adc5311
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084147B2

Verknüpfte Notizen

Wird geladen…