تفاعل #1447109

معادلة التفاعل

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

المذيبات

water

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر