Reaktion #930461

Reaktionsgleichung

water

methyl gentisate

potassium carbonate

chloropropyl trimethyl silane

→

methyl 2-hydroxy-4-(3-trimethylsilanyl-propyloxy)-benzoate

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturIt is cooled
2. 2
   ExtraktionExtraction
3. 3
   WaschenThe organic phase is washed with water
4. 4
   Trocknendried with sodium sulfate
5. 5
   Einengenconcentrated

Vorschrift

To a mixture of methyl gentisate (16.8 g, 0.1 mole) and potassium carbonate (15.2 g, 0.11 mole) in 80 ml of DMF in a nitrogen atmosphere at 80° C. is added chloropropyl trimethyl silane (16.6 g, 0.11 mole) drop by drop over a 20-minute period. The mixture is heated to 90° C. for 8 hours. It is cooled and then poured into 200 ml of water. Extraction is performed with diisopropyl ether. The organic phase is washed with water, dried with sodium sulfate, and then concentrated. After silica chromatography of the resulting yellow oil (eluent: Heptane/CH2Cl2 90:10) we obtain 3.3 g of a clean fraction of methyl 2-hydroxy-4-(3-trimethylsilanyl-propyloxy)-benzoate.

Quelle