تفاعل #64415

معادلة التفاعل

p-toluenesulfonic acid

3-methyl pentanol

sodium hydride

dimethylformamide

bromo-alcohol

→

8-(3-methylpentyloxy)octanol

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe reaction mixture is stirred at room temperature for 17 hours
2. 2
   أخرىThe reaction mixture is then partitioned between ethyl acetate and water
3. 3
   غسيلThe organic layer is washed with brine
4. 4
   تجفيفdried over Na2SO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated under vacuum
7. 7
   أخرىto give a yellow liquid
8. 8
   workup.STIRRINGthe reaction is stirred at room temperature for 16 hours
9. 9
   أخرىThe methanol is removed under reduced pressure
10. 10
    أخرىthe residue is partitioned between ethyl acetate and water
11. 11
    غسيلThe organic layer is washed with aqueous NaHCO3 and brine
12. 12
    تجفيفdried over Na2SO4
13. 13
    ترشيحfiltered
14. 14
    تركيزconcentrated under vacuum

الإجراء التجريبي

To a solution of 1.67 gms of 3-methyl pentanol in 40 ml of dimethylformamide, 0.62 gms of sodium hydride are added; and the reaction mixture is stirred at room temperature for 1 hour. To this solution is added 4.0 gms of the protected bromo-alcohol and the reaction mixture is stirred at room temperature for 17 hours. The reaction mixture is then partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to give a yellow liquid. To a solution of 4.0 gms of this liquid in 240 ml of methanol is added 0.40 gms of p-toluenesulfonic acid and the reaction is stirred at room temperature for 16 hours. The methanol is removed under reduced pressure, and the residue is partitioned between ethyl acetate and water. The organic layer is washed with aqueous NaHCO3 and brine, then dried over Na2SO4, filtered, and concentrated under vacuum to give 8-(3-methylpentyloxy)octanol.

المصدر