Dimethylformamide → 1-chloro-4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranos1-yl)-2-(4-methoxymethylethynyl-benzyl)-benzene

Participants

Reaction Conditions

Reaction Steps

1 g 1-chloro-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-[4-(trifluoromethylsulfonyloxy)-benzyl]-benzene, 2 mL triethylamine and 3 mL dimethylformamide are placed in a flask under argon atmosphere. 56 mg copper iodide, 103 mg bis-(triphenylphosphine)-palladium dichloride and finally 0.31 g methyl propargyl ether are added. The flask is tightly sealed and the mixture is stirred at 65° C. for 30 h. Then the reaction mixture is diluted with ethyl acetate and washed with 1 M hydrochloric acid. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1->2:1).

Provenance & Evidence