Reaction #1447109

Reaction equation

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

Solvents

water

Conditions

Workup

1. 1
   Otheris flushed with Ar for 5 min
2. 2
   workup.ADDITIONThen, palladium acetate (11 mg) and tricyclohexylphosphonium tetrafluoroborate (36 mg) are added
3. 3
   OtherThe flask is tightly sealed
4. 4
   TemperatureAfter 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
   Otherthe organic layer is separated
9. 9
   Washwashed with brine
10. 10
    Dryingdried (magnesium sulphate)
11. 11
    OtherThe solvent is removed under reduced pressure
12. 12
    Otherthe resulting crude product is submitted to deacetylation without further purification

Procedure

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