Reaktion #43690

Reaktionsgleichung

2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-(4-methylbenzyl)benzo[b]thiophene

ethanethiol

potassium carbonate

→

title compound

Ausbeute 32.0%

2-(β-D-Glucopyranosyl)-7-(4-methylbenzyl)benzo[b]thiophene

Ausbeute 32.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe mixture was extracted with ethyl acetate
2. 2
   WaschenThe organic layer washed with brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   SonstigeThe solvent was removed under reduced pressure
5. 5
   Sonstigethe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Vorschrift

To a solution of 2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-(4-methylbenzyl)benzo[b]thiophene (0.95 g) and ethanethiol (1.8 mL) in dichloromethane (15 mL) was added boron trifluoride diethyl ether complex (2.1 mL) at room temperature. The reaction mixture was stirred at room temperature for 3 hours, and a saturated potassium carbonate aqueous solution was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (0.16 g).

Quelle