Water → (4-Bromo-2-methyl-benzyloxy)-trimethylsilane

HRID 51795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51795
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH3:10])[CH:3]=1.C(N(CC)CC)C.Cl[Si:19]([CH3:22])([CH3:21])[CH3:20].O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:19]([CH3:22])([CH3:21])[CH3:20])=[C:4]([CH3:10])[CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 22280088(4-Bromo-2-methylphenyl)methanol2×

Produkt 1

HCID 22568853(4-Bromo-2-methyl-benzyloxy)-trimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of (4-bromo-2-methyl-phenyl)-methanol (Intermediate 133, 500.0 mg, 2.48 mmols), in 10 mL THF was added triethylamine (374.0 mg, 3.70 mmols) and chlorotrimethylsilane (297.0 mg, 2.70 mmols). The resulting solution was stirred for 17 hours at 25° C. and then treated with H2O and extracted with Et2O. The combined organic layers were washed with H2O; 10% aqueous HCl, saturated NaHCO3, and saturated NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound, 550.0 mg (81%), was isolated by column chromatography (5% EtOAc-hexanes) as a colorless oil.

Aufarbeitung

  1. extractionextracted with Et2O
  2. washThe combined organic layers were washed with H2O
  3. dry with material10% aqueous HCl, saturated NaHCO3, and saturated NaCl before being dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-73c9d9b2eb2d41caa0a2a84708d3686e
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713647B2

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