반응 #1447109

반응 방정식

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

용매

water

반응 조건

후처리

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

실험 절차

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.

출처