Potassium Hydroxide → 1-Ethynyl-2-methoxybenzene

HRID 1039207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039207
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]#[C:12][Si](C)(C)C>O.CO>[C:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][CH3:3])#[CH:12]

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 5140915((2-Methoxyphenyl)ethynyl)triMethylsilane

Produkt 1

HCID 5829121-Ethynyl-2-methoxybenzeneAusbeute 123 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Add a solution of potassium hydroxide (3.66 g, 65.2 mmol) in water (30 mL) dropwise over 30 minutes to a stirred solution of (2-methoxy-phenylethynyl)-trimethylsilane (13.2 g, 64.6 mmol) in methanol (275 mL) and stir at room temperature for 1.5 hours. Concentrate, add brine to residue, and extract with EtOAc. Dry organic layer over MgSO4 and concentrate to get 10.5 grams of a black oil. Adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 0-5% EtOAc/hexanes to afford the title compound (7.6 g, 89%).

Aufarbeitung

  1. concentrationConcentrate
  2. additionadd brine to residue
  3. extractionextract with EtOAc
  4. concentrationDry organic layer over MgSO4 and concentrate

Quellen und Nachweise

ORD-Eintrag
ord-7513f3a6b7784b878f0ad99235e19ad8
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552039B2

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