Reaktion #61411

Reaktionsgleichung

citric acid monohydrate

water

3-(β-D-glucopyranosyloxy)-4-[(4-iso-propoxyphenyl)methyl]-1-isopropyl-5-methylpyrazole

propionyl chloride

→

4-[(4-isopropoxyphenyl)methyl]-1-isopropyl-5-methyl-3-(6-O-propionyl-β-D-glucopyranosyloxy)pyrazole

Ausbeute 65.8%

Lösungsmittel

2,4,6-trimethylpyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONthe resulting mixture was purified by ODS solid phase extraction (washing solvent: distilled water, eluent: methanol)
2. 2
   SonstigeFurther purification by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Vorschrift

To a solution of 3-(β-D-glucopyranosyloxy)-4-[(4-iso-propoxyphenyl)methyl]-1-isopropyl-5-methylpyrazole (0.10 g) in 2,4,6-trimethylpyridine (1 mL) was added propionyl chloride (0.072 g) at 0° C., and the mixture was stirred for hours. To the reaction mixture were added citric acid monohydrate (3.3 g) and water, and the resulting mixture was purified by ODS solid phase extraction (washing solvent: distilled water, eluent: methanol). Further purification by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) afforded 4-[(4-isopropoxyphenyl)methyl]-1-isopropyl-5-methyl-3-(6-O-propionyl-β-D-glucopyranosyloxy)pyrazole (0.074 g)

Quelle