Water → HCID 59217793, Verbindung

HRID 2246490

Reaktionsgleichung

Reaktionsgleichung von HRID 2246490
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=1.[Br:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH:29]=[O:30].O>CCCCCC.O1CCCC1>[Br:25][C:26]1[CH:27]=[C:28]([CH:29]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=2)[OH:30])[CH:31]=[CH:32][C:33]=1[O:34][CH3:35]

Komponenten

7

Edukt 4

HCID 962WaterHCID 986623-Bromo-4-methoxybenzaldehydeHCID 57809595((4-Bromophenyl)ethynyl)triisopropylsilaneHCID 178418339Butyllithium

Produkt 1

HCID 59217793HCID 59217793, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

14.8 mL of a 1.6 M solution of n-butyllithium in hexane are added dropwise under argon to a solution of 8.0 g 1-bromo-4-triisopropylsilylethynyl-benzene in 80 mL dry tetrahydrofuran chilled to −78° C. The solution is stirred for 1 h at −70° C. Then 5.1 g 3-bromo-4-methoxy-benzaldehyde dissolved in 20 mL tetrahydrofuran are added dropwise over 15 min. The resulting solution is left in the cooling bath to warm to ambient temperature overnight. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed. The residue is purified over silica gel (cyclohexane/ethyl acetate 9:1->1:1).

Aufarbeitung

  1. additionare added dropwise over 15 min
  2. waitThe resulting solution is left in the cooling bath
  3. temperatureto warm to ambient temperature overnight
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. customthe solvent is removed
  7. customThe residue is purified over silica gel (cyclohexane/ethyl acetate 9:1->1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c585e4de99e748a285166be8d639f9b9
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687469B2

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