Reaktion #43688

Reaktionsgleichung

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

Ausbeute 69.3%

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

Ausbeute 69.3%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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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