Réaction #1447109

Équation de réaction

1-bromo-3-(4-ethylbenzyl)-2-methyl-5-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene

potassium phosphate

cyclopropylboronic acid

toluene

→

3-Cyclopropyl-5-(4-ethylbenzyl)-4-methyl-1-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene

Solvants

water

Conditions de réaction

Traitement

1. 1
   Autreis flushed with Ar for 5 min
2. 2
   workup.ADDITIONThen, palladium acetate (11 mg) and tricyclohexylphosphonium tetrafluoroborate (36 mg) are added
3. 3
   AutreThe flask is tightly sealed
4. 4
   TempératureAfter cooling to room temperature
5. 5
   workup.ADDITIONthe mixture is diluted with water and ethyl acetate
6. 6
   workup.ADDITIONtreated with charcoal
7. 7
   FiltrationAfter filtration
8. 8
   Autrethe organic layer is separated
9. 9
   Lavagewashed with brine
10. 10
    Séchagedried (magnesium sulphate)
11. 11
    AutreThe solvent is removed under reduced pressure
12. 12
    Autrethe resulting crude product is submitted to deacetylation without further purification

Mode opératoire

A flask charged with 1-bromo-3-(4-ethylbenzyl)-2-methyl-5-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene (0.30 g), potassium phosphate (0.38 g), cyclopropylboronic acid (50 mg), toluene (2 mL) and water (1 mL) is flushed with Ar for 5 min. Then, palladium acetate (11 mg) and tricyclohexylphosphonium tetrafluoroborate (36 mg) are added. The flask is tightly sealed and the mixture is stirred at 100° C. overnight. After cooling to room temperature, the mixture is diluted with water and ethyl acetate and treated with charcoal. After filtration, the organic layer is separated, washed with brine and dried (magnesium sulphate). The solvent is removed under reduced pressure and the resulting crude product is submitted to deacetylation without further purification.

Source