Chlorotrimethylsilane → 2-Trimethylsilyloxy-4-(4-(methylthio)phenyl)-3,4-dihydrofuran

HRID 1376582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376582
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.[Li]C(C)(C)C.CCCCC.[O:20]1[CH2:24][CH:23]=[CH:22][C:21]1=[O:25].[CH3:26][Si:27](Cl)([CH3:29])[CH3:28].C([O-])(O)=O.[Na+]>CCOCC.C1COCC1.[Cu]I.CCN(CC)CC>[CH3:26][Si:27]([CH3:29])([CH3:28])[O:25][CH:21]1[CH2:22][CH:23]([C:2]2[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=2)[CH2:24][O:20]1

Komponenten

11

Edukt 6

HCID 6397ChlorotrimethylsilaneHCID 8003PentaneHCID 103412(5H)-FuranoneHCID 660374-BromothioanisoleHCID 516892Sodium BicarbonateHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 184001922-Trimethylsilyloxy-4-(4-(methylthio)phenyl)-3,4-dihydrofuran

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 3.86 g (19 mmol) of 4-bromothioanisole in 90 mL of Et2O cooled at -78° C., is added 22 mL of 1.7M solution of t-BuLi in pentane (38 mmol) dropwise. The reaction mixture is stirred for 15 min at -78° C. and 3.8 g of CuI is added and the reaction mixture is allowed to warm to -40° C. over a period of 30 min. A solution of 1.7 g of 2(5H)-furanone in 10 mL of THF is added. After stirring for 1 h, 2 mL of freshly distilled TMSCl is added dropwise. The reaction mixture is then treated with 2 mL of Et3N and 50 mL of sat. NaHCO3, and extracted with 100 mL of Et2O. The Et2O layer is dried over Na2SO4 and concentrated to give the crude title compound which is used for the next step without further purification.

Aufarbeitung

  1. temperatureto warm to -40° C. over a period of 30 min
  2. stirringAfter stirring for 1 h
  3. extractionextracted with 100 mL of Et2O
  4. dry with materialThe Et2O layer is dried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dc44e7dca3934c94a0f35f803c14ead5
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663195

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