تفاعل #343679

معادلة التفاعل

diborane

tetrahydrofuran

water

tetrahydrofuran

2-methyl-2-butene

2-(2-methoxyethoxy]-1-octene

diborane

tetrahydrofuran

→

desired compound

8-[2-(2-Methoxyethoxy)ethoxy]-1-octanol

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGAfter stirring for 1/2hour
2. 2
   workup.STIRRINGThis mixture was stirred one hour at room temperature
3. 3
   workup.STIRRINGThe mixture was then stirred 2 hours
4. 4
   أخرىremoved
5. 5
   workup.STIRRINGThe remainder was stirred in an ice bath as 150 ml of 3N sodium hydroxide
6. 6
   workup.ADDITIONwas added
7. 7
   workup.ADDITIONfollowed by the slow addition of 150 ml of 30% hydrogen peroxide
8. 8
   workup.STIRRINGAfter stirring 1/2hour the mixture
9. 9
   استخلاصwas extracted with ether
10. 10
    استخلاصThe ether extract
11. 11
    غسيلwas washed in succession with saturated aqueous sodium chloride, saturated aqueous sodium bisulfite, saturated aqueous sodium chloride
12. 12
    أخرىdried
13. 13
    أخرىthe solvent removed
14. 14
    workup.DISTILLATIONThe residue was distilled on a Kugelrohr apparatus
15. 15
    أخرىThe fraction boiling at 160°-180° C., 0.2 mm was collected

الإجراء التجريبي

To 564.3 ml of 1M diborane in tetrahydrofuran was added, at 0° C. under argon with stirring, 79.16 g of 2-methyl-2-butene. After stirring for 1/2hour, 65 g of 8-[2-(2-methoxyethoxy]-1-octene was added. This mixture was stirred one hour at room temperature, then 700 ml of 1M diborane in tetrahydrofuran was added over a period of 1.5 hours. The mixture was then stirred 2 hours, then water was added and about 2/3of the tetrahydrofuran removed. The remainder was stirred in an ice bath as 150 ml of 3N sodium hydroxide was added, followed by the slow addition of 150 ml of 30% hydrogen peroxide. After stirring 1/2hour the mixture was extracted with ether. The ether extract was washed in succession with saturated aqueous sodium chloride, saturated aqueous sodium bisulfite, saturated aqueous sodium chloride, then dried and the solvent removed. The residue was distilled on a Kugelrohr apparatus. The fraction boiling at 90°-110° C., 0.2 mm was discarded. The fraction boiling at 160°-180° C., 0.2 mm was collected giving 41.3 g of the desired compound as a clear liquid.

المصدر