反応 #1447109

反応方程式

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

溶媒

water

反応条件

後処理

1. 1
   その他is flushed with Ar for 5 min
2. 2
   workup.ADDITIONThen, palladium acetate (11 mg) and tricyclohexylphosphonium tetrafluoroborate (36 mg) are added
3. 3
   その他The flask is tightly sealed
4. 4
   温度After cooling to room temperature
5. 5
   workup.ADDITIONthe mixture is diluted with water and ethyl acetate
6. 6
   workup.ADDITIONtreated with charcoal
7. 7
   ろ過After filtration
8. 8
   その他the organic layer is separated
9. 9
   洗浄washed with brine
10. 10
    乾燥dried (magnesium sulphate)
11. 11
    その他The solvent is removed under reduced pressure
12. 12
    その他the resulting crude product is submitted to deacetylation without further purification

実験手順

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.

出典