反应 #43688

反应方程式

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

收率 69.3%

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

收率 69.3%

溶剂

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   workup.STIRRINGstirred for 10 minutes
2. 2
   萃取the mixture was extracted with diethyl ether
3. 3
   洗涤The organic layer washed with brine
4. 4
   干燥dried over anhydrous magnesium sulfate
5. 5
   其他The solvent was removed under reduced pressure
6. 6
   其他the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1)

实验过程

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).

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