반응 #643963

반응 방정식

water

4-methylbenzylchloride

1-(1H-indol-6-yl)-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose

sodium hydride

→

title compound

수율 79.4%

1-[1-(4-Methylbenzyl)-1H-indol-6-yl]-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose

수율 79.4%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 2 hours
2. 2
   추출the mixture was extracted with diethyl ether
3. 3
   세척The organic layer washed with water and brine
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   기타The solvent was removed under reduced pressure
6. 6
   기타the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1)

실험 절차

To a solution of 1-(1H-indol-6-yl)-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose (0.13 g) in N,N-dimethylformamide (2 mL) was added sodium hydride (60%, 0.01 g) at 0° C., and the mixture was stirred for 10 minutes. To the mixture was added 4-methylbenzylchloride (0.032 g), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, and the mixture was extracted with diethyl ether. The organic layer washed with water and 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: n-hexane/ethyl acetate=5/1) to give the title compound (0.12 g).

출처