반응 #43688

반응 방정식

ammonium chloride

2,3,4,6-tetra-O-benzyl-D-glucono-1,5-lactone

7-(4-methylbenzyl)benzo[b]thiophene

n-butyllithium

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title compound

수율 69.3%

2,3,4,6-Tetra-O-benzyl-1-[7-(4-methylbenzyl)benzo[b]thiophen-2-yl]-D-glucopyranose

수율 69.3%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 10 minutes
2. 2
   추출the mixture was extracted with diethyl ether
3. 3
   세척The organic layer washed with 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=4/1)

실험 절차

To a solution of 7-(4-methylbenzyl)benzo[b]thiophene (0.57 g) in tetrahydrofuran (10 mL) was added n-butyllithium (2.71 mol/L tetrahydrofuran solution, 0.88 mL) at −78° C. under an argon atmosphere. The mixture was stirred at the same temperature for 30 minutes and a solution of 2,3,4,6-tetra-O-benzyl-D-glucono-1,5-lactone (1.2 g) in tetrahydrofuran (5 mL) was added to the mixture. The reaction mixture was warmed to 0° C. and stirred for 10 minutes. The reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with diethyl ether. 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: n-hexane/ethyl acetate=4/1) to give the title compound (1.2 g).

출처